Search for "high pressure" in Full Text gives 128 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2025, 21, 1388–1396, doi:10.3762/bjoc.21.103
Graphical Abstract
Figure 1: Structures of the pseudomonins D–G (1–4), pseudomonine (5), pseudomonin B (6) and salicylic acid (7...
Figure 2: Key HMBC, 1H-1H COSY and NOE correlations.
Figure 3: Extracted ion chromatogram and corresponding mass spectrum of compound 4 in the crude extract.
Figure 4: Proposed biosynthetic scheme for the formation of compounds (1–4).
Beilstein J. Org. Chem. 2025, 21, 1374–1387, doi:10.3762/bjoc.21.102
Graphical Abstract
Figure 1: Simplified schematic rendering of a high hydrostatic pressure reactor.
Scheme 1: High pressure-initiated synthesis of 1,3-dihydrobenzimidazoles 3a–d. The yields are GC yields and t...
Figure 2: Illustration of the cyclization reaction between chalcone (4) and 3-(trifluoromethyl)phenylhydrazin...
Scheme 2: High pressure-initiated catalyst- and solvent-free synthesis of pyrazoles 6a–c from chalcone (4) an...
Figure 3: Schematic representation of the cycling experiments: the major variables are the applied pressure, ...
Scheme 3: High pressure-initiated synthesis of the active pharmaceutical ingredients in Tylenol® and Aspirin®...
Scheme 4: High pressure-initiated esterification of alcohols 12a–g in a catalyst- and additional solvent-free...
Scheme 5: High pressure-initiated large scale syntheses of N-aryl- and N-alkylpyrroles at about 100 g scale.
Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89
Graphical Abstract
Figure 1: Schematic depiction of the α-CD channels containing the polyionic {[K(OH2)6]+[AuBr4]−}n chain insid...
Figure 2: Complexes of α-CD with MAuBr4 salts. Left) Co-precipitation yields from aqueous solutions of α-CD (...
Figure 3: Crystal structures of the complexes of α-CD with KAuCN2 salts, with tubular representation for α-CD...
Figure 4: Solid-state structure of the complex 2β-CD·HAuBr4·DBC. (a) Capped-stick and space-filling represent...
Figure 5: Schematic depiction of the selective removal of AuCl4− and its precipitation as solid gold from e-w...
Beilstein J. Org. Chem. 2025, 21, 999–1009, doi:10.3762/bjoc.21.81
Graphical Abstract
Figure 1: Reactivity of enamides and enamide cyclizations.
Scheme 1: Total synthesis of (−)-dihydrolycopodine and (−)-lycopodine.
Scheme 2: Collective total synthesis of fawcettimine-type alkaloids.
Scheme 3: Total syntheses of cephalotaxine and cephalezomine H.
Scheme 4: Collective total syntheses of Cephalotaxus alkaloids.
Scheme 5: Asymmetric tandem cyclization/Pictet–Spengler reaction of tertiary enamides.
Scheme 6: Tandem cyclization/Pictet–Spengler reaction for the synthesis of chiral tetracyclic compounds.
Scheme 7: Total synthesis of (−)-cephalocyclidin A.
Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80
Graphical Abstract
Figure 1: a) Tris(trichlorophenyl)methyl (TTM) radical and related trityl radicals, b) HDMO, SOMO, LUMO orbit...
Figure 2: Mixed halide tri- and perhalogenated triphenylmethyl radicals: a) Molecular structures of homo- and...
Figure 3: Pyridine-functionalized triarylmethyl radicals. a) Chemical structures of X2PyBTM, Py2MTM, and Au-F2...
Figure 4: Pyridine-functionalized triarylmethyl radicals. a) Molecular structure of Mes2F2PyBTM, and b) its f...
Figure 5: Carbazole functionalized triarylmethyl radical. a) Chemical structure of Cz-BTM and b) its energy d...
Figure 6: Donor-functionalized triphenylmethyl radicals. Molecular structures of TTM-Cz, DTM-Cz, TTM-3PCz, PT...
Figure 7: Tuning of the donor strength. Functionalization with electron-donating and electron-withdrawing gro...
Figure 8: Tuning of the donor strength, by varying the Cz-derived donor (1–36) on a TTM radical fragment. a) ...
Figure 9: Three-state model and Marcus theory: q is the charge transfer coordinate and G the free energy. Gro...
Figure 10: Dendronized carbazole donors on TTM radicals. a) Molecular structures of G3TTM and G4TTM. b) Photol...
Figure 11: Electronic extension of the Cz donor. a) Molecular structures and optoelectronic properties of TTM-...
Figure 12: Kekulé diradicals: a) hexadeca- and perchlorinated Thiele (TTH, PTH), Chichibabin (TTM-TTM, PTM-PTM...
Figure 13: Non-Kekulé diradicals: perchlorinated Schlenk–Brauns radical (m-PTH), meta-coupled TTM radicals in ...
Figure 14: UV–vis absorption and photoluminescence spectra of a) TTH in solvents of different polarity, b) dir...
Figure 15: Molecular structures of m-4BTH (meta-butylated Thiele hydrocarbon), m-4TTH (meta-trichlorinated Thi...
Figure 16: a) Polystyrene-based TTM-Cz polymer. b) Molecular structure of radical particles with backbone thro...
Figure 17: Molecular structures of polyradicals. a) Molecular structures of p-TBr6Cl3M-F8, p-TBr6Cl3M-acF8 and ...
Figure 18: Structures of coordination and metal-organic frameworks. a) Carboxylic acid functionalized monomers...
Figure 19: Structures of coordination and metal-organic frameworks. a) Molecular structures of monomers TTMDI, ...
Figure 20: Molecular structures of covalent organic frameworks m-TPM-Ph-COF, m-PTM-Ph-COF, p-TPH-COF, p-PTH-COF...
Figure 21: Molecular structures of covalent organic frameworks PTMAc-COF, oxTAMAc-COF, TOTAc-COF, PTMTAz-COF, p...
Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39
Graphical Abstract
Scheme 1: List of reactions, experimental conditions and yields studied in this work.
Figure 1: Top: 379 MHz 19F NMR spectrum of 9,10-ANTH(BnF)2 in CDCl3. Bottom: absorption (aerobic, solid line)...
Figure 2: Top: X-ray structure of 9,10-ANTH(BnF)2, thermal ellipsoids 50% probability. Bottom: a view down th...
Figure 3: Absorption spectra of ANTH and 9,10-ANTH(BnF)2 in CH2Cl2 recorded over the period of 53 days in air...
Figure 4: Direct analysis in real time (DART) positive ion mass spectrum of the photoirradiated 9,10-ANTH(BnF)...
Figure 5: The % remaining of ANTH and 9,10-ANTH(BnF)2 dissolved in CDCl3 upon irradiation. Resonances δ = 7.4...
Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33
Graphical Abstract
Figure 1: The Grotthuss–Draper, Einstein–Stark, and Beer–Lambert laws. T: transmittance; ε: molar attenuation...
Figure 2: The benefits of merging photochemistry with mechanochemical setups (top). Most common setups for ph...
Scheme 1: Mechanochemically triggered pedal-like motion in solid-state [2 + 2] photochemical cycloaddition fo...
Scheme 2: Mechanically promoted [2 + 2] photodimerization of trans-1,2-bis(4-pyridyl)ethylene (2.1) via supra...
Scheme 3: Photo-thermo-mechanosynthesis of quinolines [65].
Scheme 4: Study of the mechanically assisted [2 + 2] photodimerization of chalcone [66].
Scheme 5: Liquid-assisted vortex grinding (LAVG) for the synthesis of [2.2]paracyclophane [68].
Scheme 6: Photomechanochemical approach for the riboflavin tetraacetate-catalyzed photocatalytic oxidation of...
Scheme 7: Photomechanochemical oxidation of 1,2-diphenylethyne to benzil. The photo in Scheme 7 was republished with ...
Scheme 8: Photomechanochemical borylation of aryldiazonium salts. The photo in Scheme 8 was reproduced from [72] (© 2017 ...
Scheme 9: Photomechanochemical control over stereoselectivity in the [2 + 2] dimerization of acenaphthylene. ...
Scheme 10: Photomechanochemical synthesis of polyaromatic compounds using UV light. The photo in Scheme 10 was reproduc...
Scheme 11: Mechanically assisted photocatalytic reactions: A) atom-transfer-radical addition, B) pinacol coupl...
Scheme 12: Use of mechanoluminescent materials as photon sources for photomechanochemistry. SAOED: SrAl2O4:Eu2+...
Figure 3: SWOT (strengths, weaknesses, opportunities, threats) analysis of photomechanochemistry.
Beilstein J. Org. Chem. 2025, 21, 39–46, doi:10.3762/bjoc.21.4
Graphical Abstract
Scheme 1: Brief comparison between the main traditional synthetic routes for the preparation of substituted p...
Figure 1: The β-nitrostyrene analogues used in this work.
Scheme 2: Additional products obtained via this method: nitrobenzene and methyl benzoate are reduced in excel...
Figure 2: Numerous masses (m/z) were detected by ESI-MS at T = 0 upon mixing all the reagents to produce 1b.
Figure 3: Structures of proposed adducts. Their masses, 254.2 and 242.2, respectively, were found at T = 0 by...
Scheme 3: Proposed mechanism for the formation of the hydroxylamine side product b. N-Phenethylhydroxylamine (...
Beilstein J. Org. Chem. 2025, 21, 10–38, doi:10.3762/bjoc.21.3
Graphical Abstract
Figure 1: A high-level representation of the workflow and framework used for the optimization of organic reac...
Figure 2: (a) Photograph showing a Chemspeed HTE platform using 96-well reaction blocks. (b) Mobile robot equ...
Figure 3: (a) Description of a slug flow platform developed using segments of gas as separation medium for hi...
Figure 4: Schematic representation (a) and photograph (b) of the flow parallel synthesizer intelligently desi...
Figure 5: (a) Schematic representation of an ASFR for obtaining an optimal solution with minimal human interv...
Figure 6: (a) A modular flow platform developed for a wider variety of chemical syntheses. (b) Various catego...
Figure 7: Implementation of four complementary PATs into the optimization process of a three-step synthesis.
Figure 8: Overlay of several Raman spectra of a single condition featuring the styrene vinyl region (a) and t...
Figure 9: (a) Schematic description of the process of chemical reaction optimization through ML methods. (b) ...
Figure 10: (a) Comparison between a standard GP (single-task) and a multitask GP. Training an auxiliary task u...
Figure 11: Comparison of the reaction yield between optimizations campaign where the catalyst ligand selection...
Beilstein J. Org. Chem. 2024, 20, 2608–2634, doi:10.3762/bjoc.20.220
Graphical Abstract
Figure 1: Hierarchical assembly occurring across length scales. Molecular interactions result in fibres which...
Figure 2: Three-dimensional CLSM image of a multicomponent supramolecular structure. The three-dimensional CL...
Figure 3: AFM images of air-dried aqueous Fmoc-FF, Fmoc-S, and 1:1 Fmoc-FF:Fmoc-S solutions. Figure 3 was reprinted f...
Figure 4: (a) 3D CLSM images of macroscopically a self-sorting gel network, where all fibres were stained gre...
Figure 5: (a) 3D AFM topographic image of dried elastin fibre. (b) Indicative height and diameter profile plo...
Figure 6: The nano-to-micro imaging range of SEM and TEM [30]. Cartoons represent the nanoparticles, pores, nanow...
Figure 7: Cartoon of artifacts caused by blotting and thinning. a) Alignment of threadlike micelles (left) [32] a...
Figure 8: (a) Chemical structures of monomer compounds and a schematic of the resulting chiral helical struct...
Figure 9: Commonly observed entanglements of urea-based supramolecular helices. (a) Double helix, (b) quadrup...
Figure 10: (a) SEM image of a single three-stranded braid showing a defect in which the braid separates into s...
Figure 11: Visualization of individual atoms at 1.25 Å resolution. Three apoferritin residues are shown at hig...
Figure 12: Cartoon of a general small-angle scattering setup.
Figure 13: (a) SAXS data and fits for solution in H2O (open symbols) and D2O (closed symbols). Cryo-TEM data f...
Figure 14: (a) A cartoon illustrating the orientation phases caused by shear alignment of WLMs. (b) Rheologica...
Figure 15: (a) Chemical structure of 2NapFF and (b) a cartoon cross-section of the hollow cylinder structure f...
Figure 16: Length scales of scattering and imaging techniques [16,54,55].
Figure 17: A schematic of a hydrogel network showing the significance of various parameters extracted from SAN...
Figure 18: The morphologies of a co-assembled complex dependent on the solvent composition. Figure 18 is from [89] and was ...
Figure 19: Allowed and forbidden crossings of entangled helices. Figure 19 is from [44] and was adapted by permission from ...
Figure 20: (a) Cryo-TEM density map of self-assembled (ʟ,ʟ)-2NapFF. (b) Computational model fit to cryo-TEM ma...
Figure 21: Map showing an incomplete list of global scientific centres providing access to (a) cryo-EM in red ...
Figure 22: SANS at a range of times. Solid lines are fits to a hollow cylinder model (T = 114 min and T = 202 ...
Figure 23: SAXS data of 5 mg/mL alanine-functionalised perylene bisimide (PBI-A) in 20 v/v % MeOH at pH (a) 2;...
Figure 24: Cryo-TEM sample prepared using plunge freezing in liquid nitrogen slush and sublimed for 30 minutes...
Beilstein J. Org. Chem. 2024, 20, 2408–2420, doi:10.3762/bjoc.20.205
Graphical Abstract
Figure 1: The schematic diagram of the continuous flow microreactor system.
Scheme 1: Nitration of IO with mixed acid.
Figure 2: Two mixing setups: (a) a T-mixer and (b) a T-mixer combined with a homemade static mixer, and the e...
Figure 3:
Determination of the number of reaction orders. a) ln(1−xIO) versus t; b) versus t; c) ln(1−xIO) v...
Figure 4: Determination of (M−1)cIO0k at different temperatures and H2SO4 mass fractions. (a) 88% H2SO4, (b) ...
Figure 5: Variations and fitting of as a function of a) the mass fraction of H2SO4 at 23 °C, 40 °C, and 60 °C...
Figure 6: Determination of thermodynamic parameters n and k0 and determination of the activation energy and p...
Figure 7: a) The value of apparent rate constant k at various H2SO4 mass fractions and different temperatures...
Beilstein J. Org. Chem. 2024, 20, 1560–1571, doi:10.3762/bjoc.20.139
Graphical Abstract
Figure 1: Schematic of (a) a PEM reactor and (b) MEA.
Scheme 1: Plausible mechanism for the reduction of 1a leading to benzylamine 2a and dibenzylamine 3a.
Scheme 2: Electrochemical reduction of cyanoarenes under optimal conditions. Reaction conditions: anode catal...
Scheme 3: Scope of the electrochemical reduction of nitroarenes. Reaction conditions: anode catalyst, Pt/C; c...
Figure 2: Hypothesis of the trap of quinoline on membrane and tetrahydroquinoline and the effect of adding an...
Figure 3: Recycled use of MEA for the electroreduction of 6a in the presence of PTSA (0.10 equiv). Reaction c...
Figure 4: Recycled use of MEA for the electroreduction of 6a in the presence of PPTS (0.10 equiv). Reaction c...
Scheme 4: Scope of the electroreduction of 6 in the presence of PTSA (0.10 equiv). Reaction conditions: anode...
Scheme 5: a) Large scale synthesis of 7a and b) electoreduction of 6a using H2SO4 as a proton source.
Scheme 6: Scope of the electroreduction of 6 in the presence of PTSA (1 equiv). Reaction conditions: anode ca...
Beilstein J. Org. Chem. 2024, 20, 552–560, doi:10.3762/bjoc.20.47
Graphical Abstract
Scheme 1: Synthesis of compound 1 and N-acylated compounds 2a–c.
Figure 1: Absorption (1), fluorescence (2, λex = 410 nm) and fluorescence excitation (3, λfl = 465 nm) spectr...
Figure 2: Electronic absorption spectra of compound 2b in acetonitrile before (1) and after 15 s (2), 35 s (3...
Scheme 2: Photoisomerization of N-acylated ketoenamines 2a–c.
Figure 3: Molecular structure of O-acylated isomer 3b. Thermal ellipsoids are drawn at the 50% probability le...
Figure 4: Fragment of the molecular packing of compound 3b, showing π–π interactions in the crystalline state...
Figure 5: Absorption spectra of compound 2a in acetonitrile before (1) and after (2) the addition of Fe2+ (c2a...
Figure 6: Changes in the absorption intensity of compound 2a in acetonitrile at 520 nm after the addition of ...
Scheme 3: Sequential interaction of compounds 2a–c with Fe2+ and AcO−.
Figure 7: Job’s plot at the wavelength 429 nm, reflecting the interaction of compound 2a with Fe2+ in acetoni...
Figure 8: Fluorescence intensity of compound 2a upon alternate addition of Fe2+ and AcO−.
Beilstein J. Org. Chem. 2024, 20, 436–444, doi:10.3762/bjoc.20.38
Graphical Abstract
Figure 1: Structures of a) [10]CPP⊃C60, (b) [n+5]CPP⊃[n]CPP, and (c) [10]CPP⊃[5]CPP2+ (this work).
Figure 2: 1H NMR spectra (CD2Cl2, 25 °C) of a) a mixture of [8]–[12]CPPs and [5]CPP2+[B(C6F5)4−]2 before and aft...
Figure 3: Cyclic voltammograms of [10]CPP⊃[5]CPP2+[B(C6F5)4−]2, [10]CPP, and [5]CPP2+[B(C6F5)4−]2 in Bu4N+ B(C...
Figure 4: UV–vis–NIR spectra of [10]CPP⊃[5]CPP2+[B(C6F5)4−]2 (black), [10]CPP (blue), and [5]CPP2+[B(C6F5)4−]2...
Figure 5: Top and side view of [10]CPP⊃[5]CPP2+ complexes a) 1, b) 2, and c) 3 obtained by DFT calculation at...
Figure 6: HOMO−1, HOMO, LUMO, and LUMO+1 orbitals of [10]CPP⊃[5]CPP2+ (1), [5]CPP2+, and [10]CPP.
Figure 7: X-ray crystal structure of [10]CPP⊃[5]CPP2+[B(C6F5)4]2. a) Side and b) top views of ORTEP drawings....
Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36
Graphical Abstract
Scheme 1: Examples of BIMs used for their medicinal properties.
Scheme 2: Mechanisms for the synthesis of BIMs using protic or Lewis acids as catalysts.
Scheme 3: Synthesis of bis(indolyl)methanes using DBDMH.
Scheme 4: Competition experiments and synthesis of bis(indolyl)methanes using DBDMH.
Scheme 5: Proposed mechanism for formation of BIM of using DBDMH.
Scheme 6: Synthesis of bis(indolyl)methanes using I2.
Scheme 7: General reaction mechanism upon halogen bonding.
Scheme 8: Synthesis of bis(indolyl)methanes using I2, introduced by Ji.
Scheme 9: Synthesis of bis(indolyl)methanes using Br2 in CH3CN.
Scheme 10: Βidentate halogen-bond donors.
Scheme 11: Synthesis of bis(indolyl)methanes using bidentate halogen-bond donor 26.
Scheme 12: Proposed reaction mechanism.
Scheme 13: Synthesis of bis(indolyl)methanes using iodoalkyne as catalyst.
Scheme 14: Proposed reaction mechanism.
Scheme 15: Optimized reaction conditions used by Ramshini.
Scheme 16: Activation of the carbonyl group by HPA/TPI-Fe3O4.
Scheme 17: Synthesis of BIMs in the presence of nanoAg-Pt/SiO2-doped silicate.
Scheme 18: Mechanism of action proposed by Khalafi-Nezhad et al.
Scheme 19: Activation of the carbonyl group by the Cu–isatin Schiff base complex.
Scheme 20: Optimum reaction conditions published by Jain.
Scheme 21: Organocatalytic protocol utilizing nanoparticles introduced by Bankar.
Scheme 22: Activation of the carbonyl group by the AlCl3·6H2O-SDS-SiO2 complex.
Scheme 23: Optimal reaction conditions for the aforementioned nano-Fe3O4 based catalysts.
Scheme 24: Nanocatalytic protocol proposed by Kaur et al.
Scheme 25: Microwave approach introduced by Yuan.
Scheme 26: Microwave approach introduced by Zahran et al.
Scheme 27: Microwave irradiation protocol introduced by Bindu.
Scheme 28: Silica-supported microwave irradiation protocol.
Scheme 29: Proposed mechanism for formation of BIM by Nongkhlaw.
Scheme 30: Microwave-assisted synthesis of BIMs catalyzed by succinic acid.
Scheme 31: Proposed mechanism of action of MMO-4.
Scheme 32: Catalytic approach introduced by Muhammadpoor-Baltork et al.
Scheme 33: Reaction conditions used by Xiao-Ming.
Scheme 34: Ultrasonic irradiation-based protocol published by Saeednia.
Scheme 35: Pyruvic acid-mediated synthesis of BIMs proposed by Thopate.
Scheme 36: Synthesis of BIMs using [bmim]BF4 or [bmim]PF6 ionic liquids.
Scheme 37: Synthesis of BIMs utilizing In(OTf)3 in octylmethylimidazolium hexafluorophosphate as ionic liquid.
Scheme 38: FeCl3·6H2O-catalyzed synthesis of BIMs with use of ionic liquid.
Scheme 39: Synthesis of BIMs utilizing the [hmim]HSO4/EtOH catalytic system.
Scheme 40: Synthesis of BIMs utilizing acidic ionic liquid immobilized on silica gel (ILIS-SO2Cl).
Scheme 41: The [bmim][MeSO4]-catalyzed reaction of indole with various aldehydes.
Scheme 42: The role of [bmim][MeSO4] in catalyzing the reaction of indole with aldehydes.
Scheme 43: Synthesis of BIMs utilizing FeCl3-based ionic liquid ([BTBAC]Cl-FeCl3) as catalyst.
Scheme 44: Synthesis of BIMs using [Msim]Cl at room temperature.
Scheme 45: [Et3NH][H2PO4]-catalyzed synthesis of bis(indolyl)methanes.
Scheme 46: PILs-catalyzed synthesis of bis(indolyl)methanes.
Scheme 47: FSILs-mediated synthesis of bis(indolyl)methanes.
Scheme 48: Possible “release and catch” catalytic process.
Scheme 49: Synthesis of bis(indolyl)methanes by [DABCO-H][HSO4].
Scheme 50: Synthesis of bis(indolyl)methanes by [(THA)(SO4)].
Scheme 51: Synthesis of BBSI-Cl and BBSI-HSO4.
Scheme 52: Synthesis of BIMs in the presence of BBSI-Cl and BBSI-HSO4.
Scheme 53: Chemoselectivity of the present method.
Scheme 54: Synthesis of BIMs catalyzed by chitosan-supported ionic liquid.
Scheme 55: Proposed mechanism of action of CSIL.
Scheme 56: Optimization of the reaction in DESs.
Scheme 57: Synthesis of BIMs using ChCl/SnCl2 as DES.
Scheme 58: Synthesis of BIMs derivatives in presence of DES.
Scheme 59: BIMs synthesis in choline chloride/urea (CC/U).
Scheme 60: Flow chemistry-based synthesis of BIMs by Ley.
Scheme 61: Flow chemistry-based synthesis of BIMs proposed by Nam et al.
Scheme 62: Amino-catalyzed reaction of indole with propionaldehyde.
Scheme 63: Aminocatalytic synthesis of BIMs.
Scheme 64: Proposed mechanism for the aminocatalytic synthesis of BIMs.
Scheme 65: Enzymatic reaction of indole with aldehydes.
Scheme 66: Proposed mechanism for the synthesis of BIMs catalyzed by TLIM.
Scheme 67: Proposed reaction mechanism by Badsara.
Scheme 68: Mechanism proposed by D’Auria.
Scheme 69: Photoinduced thiourea catalysis.
Scheme 70: Proposed mechanism of photoacid activation.
Scheme 71: Proposed mechanism of action for CF3SO2Na.
Scheme 72: Proposed mechanism for the synthesis of BIMs by Mandawad.
Scheme 73: Proposed mechanism for the (a) acid generation and (b) synthesis of BIMs.
Scheme 74: a) Reaction conditions employed by Khaksar and b) activation of the carbonyl group by HFIP.
Scheme 75: Activation of the carbonyl group by the PPy@CH2Br through the formation of a halogen bond.
Scheme 76: Reaction conditions utilized by Mhaldar et al.
Scheme 77: a) Reaction conditions employed by López and b) activation of the carbonyl group by thiourea.
Scheme 78: Infrared irradiation approach introduced by Luna-Mora and his research group.
Scheme 79: Synthesis of BIMs with the use of the Fe–Zn BMOF.
Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30
Graphical Abstract
Scheme 1: “Precursor approach” for the synthesis of π-conjugated polycyclic compounds, with the thermally- or...
Scheme 2: Valence isomerization of chalcogen heteropines and subsequent cheletropic extrusion in the case of ...
Scheme 3: Early example of phenanthrene synthesis via a chemically-induced S-extrusion (and concomitant decar...
Scheme 4: Top: Conversion of dinaphthothiepine bisimides 3a,b and their sulfoxide analogues 4a,b into PBIs 6a,...
Figure 1: Top view (a) and side view (b) of the X-ray crystal structure of thiepine 3b showing its bent confo...
Scheme 5: Modular synthetic route towards dinaphthothiepines 3a–f and the corresponding S-oxides 4a–d, incorp...
Scheme 6: Top: Conversion of dithienobenzothiepine monomeric units into dithienonaphthalenes, upon S-extrusio...
Scheme 7: Synthesis of S-doped extended triphenylene derivative 22 from 3-bromothiophene (17) with the therma...
Scheme 8: Top: Synthesis of thermally-stable O-doped HBC 26a. Bottom: Synthesis of S- and Se-based soluble pr...
Scheme 9: Synthesis of dinaphthooxepine bisimide 33 and conversion into PBI 6f by O-extrusion triggered by el...
Figure 2: Cyclic voltammogram of dinaphthooxepine 33, evidencing the irreversibility of the reduction process...
Scheme 10: Top: Early example of 6-membered ring contraction with concomitant S-extrusion leading to dinaphtho...
Scheme 11: Examples of S-extrusion from annelated 1,2-dithiins under photoactivation (top) or thermal activati...
Scheme 12: Synthesis of dibenzo[1,4]dithiapentalene upon photoextrusion of SO2 [78].
Scheme 13: Extrusion of SO in naphthotrithiin-2-oxides for the synthesis of 2,5-dihydrothiophene 1-oxides [79].
Scheme 14: SO-extrusion as a key step in the synthesis of fullerenes (C60 and C70) encapsulating H2 molecules [80,82]....
Scheme 15: Synthesis of diepoxytetracene precursor 56 and its on-surface conversion into tetracene upon O-extr...
Scheme 16: Soluble precursors of hexacene, decacene and dodecacene incorporating 1,4-epoxides in their hydroca...
Scheme 17: Synthesis of tetraepoxide 59 as soluble precursor of decacene [85].
Figure 3: Constant-height STM measurement of decacene on Au(111) using a CO-functionalized tip (sample voltag...
Beilstein J. Org. Chem. 2024, 20, 101–117, doi:10.3762/bjoc.20.11
Graphical Abstract
Scheme 1: Photoinduced formation of benzo[c]quinolizinium and its interaction with DNA upon intercalation.
Scheme 2: Synthesis of styrylpyridine derivatives 2a–g. Conditions: i: piperidine, MeOH, reflux (2a,c), ii: C...
Figure 1: Absorption spectra of styrylpyridine derivatives 2a (black), 2b (red), 2c (blue), 2d (green), 2e (m...
Figure 2: Changes of the absorption spectra during the irradiation of 2a in MeCN for 16 min (A), 2b in MeCN f...
Figure 3: Changes of the absorption spectra during the irradiation of 2c for 13 min (A), 2d for 12 min (B), 2e...
Scheme 3: Photoinduced formation of styrylpyridine derivatives 2b–g to the benzo[c]quinolizinium ions 3b–g (y...
Figure 4: Photometric titration of ct DNA to 3c (A) 3e (B) 3f (C) and 3g (D) (c = 20 µM) in Na phosphate buff...
Figure 5: Fluorimetric titration of ct DNA to 3c (A), 3e (B), 3f (C), and 3g (D) (c = 20 µM) in Na phosphate ...
Figure 6: CD (A) and LD (B) spectra of 3f and ct DNA (cDNA = 20 µM) in Na phosphate buffer (pH 7.0, T = 20 °C...
Figure 7: Changes of the absorption (A) and CD (B) spectra during the irradiation of 2e (1) and 2f (2) (c = 2...
Scheme 4: Proposed mechanisms for the photoinduced DNA damage initiated by photoexcitation of benzoquinolizin...
Beilstein J. Org. Chem. 2023, 19, 1858–1866, doi:10.3762/bjoc.19.138
Graphical Abstract
Scheme 1: Reaction of the La@C2v-C82 anion with benzyl bromide derivatives.
Figure 1: Changes in absorption spectra during the reaction of La@C2v-C82 anion with 1a.
Figure 2: HPLC profiles of the reaction mixture. Conditions: Buckyprep column (⌀ = 4.6 × 250 mm); eluent, tol...
Figure 3: HPLC profiles (Buckyprep column (⌀ = 4.6 × 250 mm); eluent, toluene; flow rate, 1.0 mL/min; UV dete...
Figure 4: Absorption spectra of 2, 3, 4, and 5 in CS2 and absorption spectra of C14, C10, C18, and C9 in Ce@C2...
Figure 5: ORTEP drawing of 3a with thermal ellipsoids shown at 50% probability level. Only an independent uni...
Figure 6: (a) Charge density of La@C2v-C82 anion as a function of its POAV values and (b) an enlarged part vi...
Beilstein J. Org. Chem. 2023, 19, 789–799, doi:10.3762/bjoc.19.59
Graphical Abstract
Figure 1: Structures of compounds 1–9.
Figure 2: Key 1H–1H COSY, HMBC, and ROESY correlations of compounds 1–4, 7, and 8.
Figure 3: Calculated and experimental ECD spectra of compounds 1 and 4.
Figure 4: Biological evaluation. Compounds 3‒5 inhibited the expression of LPS-induced pro-inflammatory expre...
Beilstein J. Org. Chem. 2023, 19, 245–281, doi:10.3762/bjoc.19.23
Graphical Abstract
Figure 1: Examples of terpenes containing a bicyclo[3.6.0]undecane motif.
Figure 2: Commercially available first and second generation Grubbs and Hoveyda–Grubbs catalysts.
Figure 3: Examples of strategies to access the fusicoccan and ophiobolin tricyclic core structure by RCM.
Scheme 1: Synthesis of bicyclic core structure 12 of ophiobolin M (13) and cycloaraneosene (14).
Scheme 2: Synthesis of the core structure 21 of ophiobolins and fusicoccanes.
Scheme 3: Ring-closing metathesis attempts starting from thioester 22.
Scheme 4: Total synthesis of ent-fusicoauritone (28).
Figure 4: General structure of ophiobolins and congeners.
Scheme 5: Total synthesis of (+)-ophiobolin A (8).
Scheme 6: Investigation of RCM for the synthesis of ophiobolin A (8). Path A) RCM with TBDPS-protected alcoho...
Scheme 7: Synthesis of the core structure of cotylenin A aglycon, cotylenol (50).
Scheme 8: Synthesis of tricyclic core structure of fusicoccans.
Scheme 9: Total synthesis of (−)-teubrevin G (59).
Scheme 10: Synthesis of the core skeleton 63 of the basmane family.
Scheme 11: Total synthesis of (±)-schindilactone A (68).
Scheme 12: Total synthesis of dactylol (72).
Scheme 13: Ring-closing metathesis for the total synthesis of (±)-asteriscanolide (2).
Scheme 14: Synthesis of the simplified skeleton of pleuromutilin (1).
Scheme 15: Total synthesis of (−)-nitidasin (93) using a ring-closing metathesis to construct the eight-member...
Scheme 16: Total synthesis of (±)-naupliolide (97).
Scheme 17: Synthesis of the A-B ring structure of fusicoccane (101).
Scheme 18: First attempts of TRCM of dienyne substrates.
Scheme 19: TRCM on optimized substrates towards the synthesis of ophiobolin A (8).
Scheme 20: Tandem ring-closing metathesis for the synthesis of variecolin intermediates 114 and 115.
Scheme 21: Synthesis of poitediol (118) using the allylsilane ring-closing metathesis.
Scheme 22: Access to scaffold 122 by a NHK coupling reaction.
Scheme 23: Key step to construct the [5-8] bicyclooctanone core of aquatolide (4).
Scheme 24: Initial strategy to access aquatolide (4).
Scheme 25: Synthetic plan to cotylenin A (130).
Scheme 26: [5-8] Bicyclic structure of brachialactone (7) constructed by a Mizoroki–Heck reaction.
Scheme 27: Influence of the replacement of the allylic alcohol moiety.
Scheme 28: Formation of variecolin intermediate 140 through a SmI2-mediated Barbier-type reaction.
Scheme 29: SmI2-mediated ketyl addition. Pleuromutilin (1) eight-membered ring closure via C5–C14 bond formati...
Scheme 30: SmI2-mediated dialdehyde cyclization cascade of [5-8-6] pleuromutilin scaffold 149.
Scheme 31: A) Modular synthetic route to mutilin and pleuromutilin family members by Herzon’s group. B) Scaffo...
Scheme 32: Photocatalyzed oxidative ring expansion in pleuromutilin (1) total synthesis.
Scheme 33: Reductive radical cascade cyclization route towards (−)-6-epi-ophiobolin N (168).
Scheme 34: Reductive radical cascade cyclization route towards (+)-6-epi-ophiobolin A (173).
Scheme 35: Radical 8-endo-trig-cyclization of a xanthate precursor.
Figure 5: Structural representations of hypoestin A (177), albolic acid (178), and ceroplastol II (179) beari...
Scheme 36: Synthesis of the common [5-8-5] tricyclic intermediate of hypoestin A (177), albolic acid (178), an...
Scheme 37: Asymmetric synthesis of hypoestin A (177), albolic acid (178), and ceroplastol II (179).
Figure 6: Scope of the Pauson–Khand reaction.
Scheme 38: Nazarov cyclization revealing the fusicoauritone core structure 192.
Scheme 39: Synthesis of fusicoauritone (28) through Nazarov cyclization.
Scheme 40: (+)-Epoxydictymene (5) synthesis through a Nicholas cyclization followed by a Pauson–Khand reaction...
Scheme 41: Synthesis of aquatolide (4) by a Mukaiyama-type aldolisation.
Scheme 42: Tandem Wolff/Cope rearrangement furnishing the A-B bicyclic moiety 204 of variecolin.
Scheme 43: Asymmetric synthesis of the A-B bicyclic core 205 and 206 of variecolin.
Scheme 44: Formation of [5-8]-fused rings by cyclization under thermal activation.
Scheme 45: Construction of the [5-8-6] tricyclic core structure of variecolin (3) by Diels–Alder reaction.
Scheme 46: Synthesis of the [6-4-8-5]-tetracyclic skeleton by palladium-mediated cyclization.
Scheme 47: Access to the [5-8] bicyclic core structure of asteriscanolide (227) through rhodium-catalyzed cycl...
Scheme 48: Total syntheses of asterisca-3(15),6-diene (230) and asteriscanolide (2) with a Rh-catalyzed cycliz...
Scheme 49: Photocyclization of 2-pyridones to access the [5-8-5] backbone of fusicoccanes.
Scheme 50: Total synthesis of (+)-asteriscunolide D (245) and (+)-aquatolide (4) through photocyclization.
Scheme 51: Biocatalysis pathway to construct the [5-8-5] tricyclic scaffold of brassicicenes.
Scheme 52: Influence of the CotB2 mutant over the cyclization’s outcome of GGDP.
Beilstein J. Org. Chem. 2022, 18, 688–706, doi:10.3762/bjoc.18.70
Graphical Abstract
Figure 1: Inductive heating, a powerful tool in industry and the Life Sciences.
Figure 2: Electric displacement field of a ferromagnetic and superparamagnetic material.
Figure 3: Temperature profiles of reactors heated conventionally and by RF heating (Figure 3 redrawn from [24]).
Scheme 1: Continuous flow synthesis of isopulegol (2) from citronellal (1).
Scheme 2: Dry (reaction 1) and steam (reaction 2) methane reforming.
Scheme 3: Calcination and RF heating.
Scheme 4: The continuously operated “Sabatier” process.
Scheme 5: Biofuel production from biomass using inductive heating for pyrolysis.
Scheme 6: Water electrolysis using an inductively heated electrolysis cell.
Scheme 7: Dimroth rearrangement (reaction 1) and three-component reaction (reaction 2) to propargyl amines 8 ...
Figure 4: A. Flow reactor filled with magnetic nanostructured particles (MagSilicaTM) and packed bed reactor ...
Scheme 8: Claisen rearrangement in flow: A. comparison between conventional heating (external oil bath), micr...
Scheme 9: Continuous flow reactions and comparison with batch reaction (oil bath). A. Pd-catalyzed transfer h...
Scheme 10: Continuous flow reactions and comparison with batch reaction (oil bath). A. pericyclic reactions an...
Scheme 11: Reactions under flow conditions using inductively heated fixed-bed materials serving as stoichiomet...
Scheme 12: Reactions under flow conditions using inductively heated fixed-bed materials serving as catalysts: ...
Scheme 13: Two step flow protocol for the preparation of 1,1'-diarylalkanes 77 from ketones and aldehydes 74, ...
Scheme 14: O-Alkylation, the last step in the multistep flow synthesis of Iloperidone (80) accompanied with a ...
Scheme 15: Continuous two-step flow process consisting of Grignard reaction followed by water elimination bein...
Scheme 16: Inductively heated continuous flow protocol for the synthesis of Iso E Super (88) [91,92].
Scheme 17: Three-step continuous flow synthesis of macrocycles 89 and 90 with musk-like olfactoric properties.
Beilstein J. Org. Chem. 2022, 18, 567–579, doi:10.3762/bjoc.18.59
Graphical Abstract
Figure 1: Reaction sequence starting from GlcNAc with ManNAc as an intermediate. Pyr is added in the second s...
Figure 2: Enzyme loading after immobilization of the epimerase and aldolase on different carriers.
Figure 3: Evaluation of immobilized epimerase on different carriers with respect to specific activity. Reacti...
Figure 4: Evaluation of immobilized aldolase on different carriers with respect to specific activity. Reactio...
Figure 5: Relative activities in repetitive batch experiments of the immobilized epimerase on polymethacrylat...
Figure 6: Relative activities in repetitive batch experiments of the immobilized aldolase on amino methacryla...
Figure 7: Recycling study of immobilized epimerase and aldolase. Assay conditions: 100 mM Tris, pH 8, 40 °C, ...
Figure 8: Measured reaction rates of the immobilized epimerase. The dashed line is the fit according to the M...
Figure 9: Measured reaction rate of the immobilized epimerase as a function of pyruvate and pressure. Dashed ...
Figure 10: Measured reaction rate (left) and the determined inhibition constant by pyruvate (right) at differe...
Figure 11: Measured kinetics of the aldolase when varying the pyruvate and ManNAc concentration (given in mM) ...
Figure 12: Circular reactor, vessel mixing was achieved with a magnetic stirrer and samples were taken directl...
Figure 13: Aldolase: Change of the equilibrium constant at different pressures. Starting concentrations were v...
Figure 14: Progress curve of the circular reactor with both reactions at varying pressures. Starting condition...
Figure 15: Residence time distributions of the stand-alone system and the reactor integrated into the system. ...
Figure 16: Reactor set-up (left to right): UHPLC pump, heated fixed-bed reactor, capillaries (ID: 25 µm or 50 ...
Beilstein J. Org. Chem. 2021, 17, 2726–2728, doi:10.3762/bjoc.17.184
Beilstein J. Org. Chem. 2021, 17, 2340–2347, doi:10.3762/bjoc.17.152
Graphical Abstract
Figure 1: Biologically active phenanthridines.
Figure 2: Synthetic routes to phenanthridines via iminyl radicals.
Scheme 1: Previous unexpected synthesis of the phenanthridine framework.
Scheme 2: Synthesis of biaryl benzaldehydes.
Scheme 3: Synthesis of biaryl oximes.
Scheme 4: Synthesis of phenanthridines. Reagents and conditions (i) UV irradiation (450 W medium pressure Hg ...
Figure 3: Two possible mechanistic routes and intermediates in the synthesis of phenanthridines.
Scheme 5: Synthesis of trisphaeridine. Reagents and conditions (i) cat. Pd(PPh3)4, aq Na2CO3, DME, reflux, Ar...
Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90
Graphical Abstract
Figure 1: Representative shares of the global F&F market (2018) segmented on their applications [1].
Figure 2: General structure of an international fragrance company [2].
Figure 3: The Michael Edwards fragrance wheel.
Figure 4: Examples of oriental (1–3), woody (4–7), fresh (8–10), and floral (11 and 12) notes.
Figure 5: A basic depiction of batch vs flow.
Scheme 1: Examples of reactions for which flow processing outperforms batch.
Scheme 2: Some industrially important aldol-based transformations.
Scheme 3: Biphasic continuous aldol reactions of acetone and various aldehydes.
Scheme 4: Aldol synthesis of 43 in flow using LiHMDS as the base.
Scheme 5: A semi-continuous synthesis of doravirine (49) involving a key aldol reaction.
Scheme 6: Enantioselective aldol reaction using 5-(pyrrolidin-2-yl)tetrazole (51) as catalyst in a microreact...
Scheme 7: Gröger's example of asymmetric aldol reaction in aqueous media.
Figure 6: Immobilised reagent column reactor types.
Scheme 8: Photoinduced thiol–ene coupling preparation of silica-supported 5-(pyrrolidin-2-yl)tetrazole 63 and...
Scheme 9: Continuous-flow approach for enantioselective aldol reactions using the supported catalyst 67.
Scheme 10: Ötvös’ employment of a solid-supported peptide aldol catalyst in flow.
Scheme 11: The use of proline tetrazole packed in a column for aldol reaction between cyclohexanone (65) and 2...
Scheme 12: Schematic diagram of an aminosilane-grafted Si-Zr-Ti/PAI-HF reactor for continuous-flow aldol and n...
Scheme 13: Continuous-flow condensation for the synthesis of the intermediate 76 to nabumetone (77) and Microi...
Scheme 14: Synthesis of ψ-Ionone (80) in continuous-flow via aldol condensation between citral (79) and aceton...
Scheme 15: Synthesis of β-methyl-ionones (83) from citral (79) in flow. The steps are separately described, an...
Scheme 16: Continuous-flow synthesis of 85 from 84 described by Gavriilidis et al.
Scheme 17: Continuous-flow scCO2 apparatus for the synthesis of 2-methylpentanal (87) and the self-condensed u...
Scheme 18: Chen’s two-step flow synthesis of coumarin (90).
Scheme 19: Pechmann condensation for the synthesis of 7-hydroxyxcoumarin (93) in flow. The setup extended to c...
Scheme 20: Synthesis of the dihydrojasmonate 35 exploiting nitro derivative proposed by Ballini et al.
Scheme 21: Silica-supported amines as heterogeneous catalyst for nitroaldol condensation in flow.
Scheme 22: Flow apparatus for the nitroaldol condensation of p-hydroxybenzaldehyde (102) to nitrostyrene 103 a...
Scheme 23: Nitroaldol reaction of 64 to 105 employing a quaternary ammonium functionalised PANF.
Scheme 24: Enantioselective nitroaldol condensation for the synthesis of 108 under flow conditions.
Scheme 25: Enatioselective synthesis of 1,2-aminoalcohol 110 via a copper-catalysed nitroaldol condensation.
Scheme 26: Examples of Knoevenagel condensations applied for fragrance components.
Scheme 27: Flow apparatus for Knoevenagel condensation described in 1989 by Venturello et al.
Scheme 28: Knoevenagel reaction using a coated multichannel membrane microreactor.
Scheme 29: Continuous-flow apparatus for Knoevenagel condensation employing sugar cane bagasse as support deve...
Scheme 30: Knoevenagel reaction for the synthesis of 131–135 in flow using an amine-functionalised silica gel. ...
Scheme 31: Continuous-flow synthesis of compound 137, a key intermediate for the synthesis of pregabalin (138)...
Scheme 32: Continuous solvent-free apparatus applied for the synthesis of compounds 140–143 using a TSE. Throu...
Scheme 33: Lewis et al. developed a spinning disc reactor for Darzens condensation of 144 and a ketone to furn...
Scheme 34: Some key industrial applications of conjugate additions in the F&F industry.
Scheme 35: Continuous-flow synthesis of 4-(2-hydroxyethyl)thiomorpholine 1,1-dioxide (156) via double conjugat...
Scheme 36: Continuous-flow system for Michael addition using CsF on alumina as the catalyst.
Scheme 37: Calcium chloride-catalysed asymmetric Michael addition using an immobilised chiral ligand.
Scheme 38: Continuous multistep synthesis for the preparation of (R)-rolipram (173). Si-NH2: primary amine-fun...
Scheme 39: Continuous-flow Michael addition using ion exchange resin Amberlyst® A26.
Scheme 40: Preparation of the heterogeneous catalyst 181 developed by Paixão et al. exploiting Ugi multicompon...
Scheme 41: Continuous-flow system developed by the Paixão’s group for the preparation of Michael asymmetric ad...
Scheme 42: Continuous-flow synthesis of nitroaldols catalysed by supported catalyst 184 developed by Wennemers...
Scheme 43: Heterogenous polystyrene-supported catalysts developed by Pericàs and co-workers.
Scheme 44: PANF-supported pyrrolidine catalyst for the conjugate addition of cyclohexanone (65) and trans-β-ni...
Scheme 45: Synthesis of (−)-paroxetine precursor 195 developed by Ötvös, Pericàs, and Kappe.
Scheme 46: Continuous-flow approach for the 5-step synthesis of (−)-oseltamivir (201) as devised by Hayashi an...
Scheme 47: Continuous-flow enzyme-catalysed Michael addition.
Scheme 48: Continuous-flow copper-catalysed 1,4 conjugate addition of Grignard reagents to enones. Reprinted w...
Scheme 49: A collection of commonly encountered hydrogenation reactions.
Figure 7: The ThalesNano H-Cube® continuous-flow hydrogenator.
Scheme 50: Chemoselective reduction of an α,β-unsaturated ketone using the H-Cube® reactor.
Scheme 51: Incorporation of Lindlar’s catalyst into the H-Cube® reactor for the reduction of an alkyne.
Scheme 52: Continuous-flow semi-hydrogenation of alkyne 208 to 209 using SACs with H-Cube® system.
Figure 8: The standard setups for tube-in-tube gas–liquid reactor units.
Scheme 53: Homogeneous hydrogenation of olefins using a tube-in-tube reactor setup.
Scheme 54: Recyclable heterogeneous flow hydrogenation system.
Scheme 55: Leadbeater’s reverse tube-in-tube hydrogenation system for olefin reductions.
Scheme 56: a) Hydrogenation using a Pd-immobilised microchannel reactor (MCR) and b) a representation of the i...
Scheme 57: Hydrogenation of alkyne 238 exploiting segmented flow in a Pd-immobilised capillary reactor.
Scheme 58: Continuous hydrogenation system for the preparation of cyrene (241) from (−)-levoglucosenone (240).
Scheme 59: Continuous hydrogenation system based on CSMs developed by Hornung et al.
Scheme 60: Chemoselective reduction of carbonyls (ketones over aldehydes) in flow.
Scheme 61: Continuous system for the semi-hydrogenation of 256 and 258, developed by Galarneau et al.
Scheme 62: Continuous synthesis of biodiesel fuel 261 from lignin-derived furfural acetone (260).
Scheme 63: Continuous synthesis of γ-valerolacetone (263) via CTH developed by Pineda et al.
Scheme 64: Continuous hydrogenation of lignin-derived biomass (products 265, 266, and 267) using a sustainable...
Scheme 65: Ru/C or Rh/C-catalysed hydrogenation of arene in flow as developed by Sajiki et al.
Scheme 66: Polysilane-immobilized Rh–Pt-catalysed hydrogenation of arenes in flow by Kobayashi et al.
Scheme 67: High-pressure in-line mixing of H2 for the asymmetric reduction of 278 at pilot scale with a 73 L p...
Figure 9: Picture of the PFR employed at Eli Lilly & Co. for the continuous hydrogenation of 278 [287]. Reprinted ...
Scheme 68: Continuous-flow asymmetric hydrogenation using Oppolzer's sultam 280 as chiral auxiliary.
Scheme 69: Some examples of industrially important oxidation reactions in the F&F industry. CFL: compact fluor...
Scheme 70: Gold-catalysed heterogeneous oxidation of alcohols in flow.
Scheme 71: Uozumi’s ARP-Pt flow oxidation protocol.
Scheme 72: High-throughput screening of aldehyde oxidation in flow using an in-line GC.
Scheme 73: Permanganate-mediated Nef oxidation of nitroalkanes in flow with the use of in-line sonication to p...
Scheme 74: Continuous-flow aerobic anti-Markovnikov Wacker oxidation.
Scheme 75: Continuous-flow oxidation of 2-benzylpyridine (312) using air as the oxidant.
Scheme 76: Continuous-flow photo-oxygenation of monoterpenes.
Scheme 77: A tubular reactor design for flow photo-oxygenation.
Scheme 78: Glucose oxidase (GOx)-mediated continuous oxidation of glucose using compressed air and the FFMR re...
Scheme 79: Schematic continuous-flow sodium hypochlorite/TEMPO oxidation of alcohols.
Scheme 80: Oxidation using immobilised TEMPO (344) was developed by McQuade et al.
Scheme 81: General protocol for the bleach/catalytic TBAB oxidation of aldehydes and alcohols.
Scheme 82: Continuous-flow PTC-assisted oxidation using hydrogen peroxide. The process was easily scaled up by...
Scheme 83: Continuous-flow epoxidation of cyclohexene (348) and in situ preparation of m-CPBA.
Scheme 84: Continuous-flow epoxidation using DMDO as oxidant.
Scheme 85: Mukayama aerobic epoxidation optimised in flow mode by the Favre-Réguillon group.
Scheme 86: Continuous-flow asymmetric epoxidation of derivatives of 359 exploiting a biomimetic iron catalyst.
Scheme 87: Continuous-flow enzymatic epoxidation of alkenes developed by Watts et al.
Scheme 88: Engineered multichannel microreactor for continuous-flow ozonolysis of 366.
Scheme 89: Continuous-flow synthesis of the vitamin D precursor 368 using multichannel microreactors. MFC: mas...
Scheme 90: Continuous ozonolysis setup used by Kappe et al. for the synthesis of various substrates employing ...
Scheme 91: Continuous-flow apparatus for ozonolysis as developed by Ley et al.
Scheme 92: Continuous-flow ozonolysis for synthesis of vanillin (2) using a film-shear flow reactor.
Scheme 93: Examples of preparative methods for ajoene (386) and allicin (388).
Scheme 94: Continuous-flow oxidation of thioanisole (389) using styrene-based polymer-supported peroxytungstat...
Scheme 95: Continuous oxidation of thiosulfinates using Oxone®-packed reactor.
Scheme 96: Continuous-flow electrochemical oxidation of thioethers.
Scheme 97: Continuous-flow oxidation of 400 to cinnamophenone (235).
Scheme 98: Continuous-flow synthesis of dehydrated material 401 via oxidation of methyl dihydrojasmonate (33).
Scheme 99: Some industrially important transformations involving Grignard reagents.
Scheme 100: Grachev et al. apparatus for continuous preparation of Grignard reagents.
Scheme 101: Example of fluidized Mg bed reactor with NMR spectrometer as on-line monitoring system.
Scheme 102: Continuous-flow synthesis of Grignard reagents and subsequent quenching reaction.
Figure 10: Membrane-based, liquid–liquid separator with integrated pressure control [52]. Adapted with permission ...
Scheme 103: Continuous-flow synthesis of 458, an intermediate to fluconazole (459).
Scheme 104: Continuous-flow synthesis of ketones starting from benzoyl chlorides.
Scheme 105: A Grignard alkylation combining CSTR and PFR technologies with in-line infrared reaction monitoring....
Scheme 106: Continuous-flow preparation of 469 from Grignard addition of methylmagnesium bromide.
Scheme 107: Continuous-flow synthesis of Grignard reagents 471.
Scheme 108: Preparation of the Grignard reagent 471 using CSTR and the continuous process for synthesis of the ...
Scheme 109: Continuous process for carboxylation of Grignard reagents in flow using tube-in-tube technology.
Scheme 110: Continuous synthesis of propargylic alcohols via ethynyl-Grignard reagent.
Scheme 111: Silica-supported catalysed enantioselective arylation of aldehydes using Grignard reagents in flow ...
Scheme 112: Acid-catalysed rearrangement of citral and dehydrolinalool derivatives.
Scheme 113: Continuous stilbene isomerisation with continuous recycling of photoredox catalyst.
Scheme 114: Continuous-flow synthesis of compound 494 as developed by Ley et al.
Scheme 115: Selected industrial applications of DA reaction.
Scheme 116: Multistep flow synthesis of the spirocyclic structure 505 via employing DA cycloaddition.
Scheme 117: Continuous-flow DA reaction developed in a plater flow reactor for the preparation of the adduct 508...
Scheme 118: Continuous-flow DA reaction using a silica-supported imidazolidinone organocatalyst.
Scheme 119: Batch vs flow for the DA reaction of (cyclohexa-1,5-dien-1-yloxy)trimethylsilane (513) with acrylon...
Scheme 120: Continuous-flow DA reaction between 510 and 515 using a shell-core droplet system.
Scheme 121: Continuous-flow synthesis of bicyclic systems from benzyne precursors.
Scheme 122: Continuous-flow synthesis of bicyclic scaffolds 527 and 528 for further development of potential ph...
Scheme 123: Continuous-flow inverse-electron hetero-DA reaction to pyridine derivatives such as 531.
Scheme 124: Comparison between batch and flow for the synthesis of pyrimidinones 532–536 via retro-DA reaction ...
Scheme 125: Continuous-flow coupled with ultrasonic system for preparation of ʟ-ascorbic acid derivatives 539 d...
Scheme 126: Two-step continuous-flow synthesis of triazole 543.
Scheme 127: Continuous-flow preparation of triazoles via CuAAC employing 546-based heterogeneous catalyst.
Scheme 128: Continuous-flow synthesis of compounds 558 through A3-coupling and 560 via AgAAC both employing the...
Scheme 129: Continuous-flow photoinduced [2 + 2] cycloaddition for the preparation of bicyclic derivatives of 5...
Scheme 130: Continuous-flow [2 + 2] and [5 + 2] cycloaddition on large scale employing a flow reactor developed...
Scheme 131: Continuous-flow preparation of the tricyclic structures 573 and 574 starting from pyrrole 570 via [...
Scheme 132: Continuous-flow [2 + 2] photocyclization of cinnamates.
Scheme 133: Continuous-flow preparation of cyclobutane 580 on a 5-plates photoreactor.
Scheme 134: Continuous-flow [2 + 2] photocycloaddition under white LED lamp using heterogeneous PCN as photocat...
Figure 11: Picture of the parallel tube flow reactor (PTFR) "The Firefly" developed by Booker-Milburn et al. a...
Scheme 135: Continuous-flow acid-catalysed [2 + 2] cycloaddition between silyl enol ethers and acrylic esters.
Scheme 136: Continuous synthesis of lactam 602 using glass column reactors.
Scheme 137: In situ generation of ketenes for the Staudinger lactam synthesis developed by Ley and Hafner.
Scheme 138: Application of [2 + 2 + 2] cycloadditions in flow employed by Ley et al.
Scheme 139: Examples of FC reactions applied in F&F industry.
Scheme 140: Continuous-flow synthesis of ibuprofen developed by McQuade et al.
Scheme 141: The FC acylation step of Jamison’s three-step ibuprofen synthesis.
Scheme 142: Synthesis of naphthalene derivative 629 via FC acylation in microreactors.
Scheme 143: Flow system for rapid screening of catalysts and reaction conditions developed by Weber et al.
Scheme 144: Continuous-flow system developed by Buorne, Muller et al. for DSD optimisation of the FC acylation ...
Scheme 145: Continuous-flow FC acylation of alkynes to yield β-chlorovinyl ketones such as 638.
Scheme 146: Continuous-flow synthesis of tonalide (619) developed by Wang et al.
Scheme 147: Continuous-flow preparation of acylated arene such as 290 employing Zr4+-β-zeolite developed by Kob...
Scheme 148: Flow system applied on an Aza-FC reaction catalysed by the thiourea catalyst 648.
Scheme 149: Continuous hydroformylation in scCO2.
Scheme 150: Two-step flow synthesis of aldehyde 655 through a sequential Heck reaction and subsequent hydroform...
Scheme 151: Single-droplet (above) and continuous (below) flow reactors developed by Abolhasani et al. for the ...
Scheme 152: Continuous hydroformylation of 1-dodecene (655) using a PFR-CSTR system developed by Sundmacher et ...
Scheme 153: Continuous-flow synthesis of the aldehyde 660 developed by Eli Lilly & Co. [32]. Adapted with permissio...
Scheme 154: Continuous asymmetric hydroformylation employing heterogenous catalst supported on carbon-based sup...
Scheme 155: Examples of acetylation in F&F industry: synthesis of bornyl (S,R,S-664) and isobornyl (S,S,S-664) ...
Scheme 156: Continuous-flow preparation of bornyl acetate (S,R,S-664) employing the oscillating flow reactor.
Scheme 157: Continuous-flow synthesis of geranyl acetate (666) from acetylation of geraniol (343) developed by ...
Scheme 158: 12-Ttungstosilicic acid-supported silica monolith-catalysed acetylation in flow.
Scheme 159: Continuous-flow preparation of cyclopentenone 676.
Scheme 160: Two-stage synthesis of coumarin (90) via acetylation of salicylaldehyde (88).
Scheme 161: Intensification process for acetylation of 5-methoxytryptamine (677) to melatonin (678) developed b...
Scheme 162: Examples of macrocyclic musky odorants both natural (679–681) and synthetic (682 and 683).
Scheme 163: Flow setup combined with microwave for the synthesis of macrocycle 686 via RCM.
Scheme 164: Continuous synthesis of 2,5-dihydro-1H-pyrroles via ring-closing metathesis.
Scheme 165: Continuous-flow metathesis of 485 developed by Leadbeater et al.
Figure 12: Comparison between RCM performed using different routes for the preparation of 696. On the left the...
Scheme 166: Continuous-flow RCM of 697 employed the solid-supported catalyst 698 developed by Grela, Kirschning...
Scheme 167: Continuous-flow RORCM of cyclooctene employing the silica-absorbed catalyst 700.
Scheme 168: Continuous-flow self-metathesis of methyl oleate (703) employing SILP catalyst 704.
Scheme 169: Flow apparatus for the RCM of 697 using a nanofiltration membrane for the recovery and reuse of the...
Scheme 170: Comparison of loadings between RCMs performed with different routes for the synthesis of 709.