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Controlled oligomerization of [1.1.1]propellane through radical polarity matching: selective synthesis of SF5- and CF3SF4-containing [2]staffanes
- Jón Atiba Buldt,
- Wang-Yeuk Kong,
- Yannick Kraemer,
- Masiel M. Belsuzarri,
- Ansh Hiten Patel,
- James C. Fettinger,
- Dean J. Tantillo and
- Cody Ross Pitts
Beilstein J. Org. Chem. 2024, 20, 3134–3143, doi:10.3762/bjoc.20.259
Graphical Abstract
Figure 1: (Top) highlighting selectivity challenges in the synthesis of [n]staffanes using excess [1.1.1]prop...
Figure 2: Computed free energy profile for the oligomerization of [1.1.1]propellane (1) following SF5 radical...
Figure 3: Computed free energy profile for the oligomerization of [1.1.1]propellane (1) following CF3SF4 radi...
Figure 4: (A) The molecular structure of 3 at 90 K with 5 independent moieties in the asymmetric axis viewed ...
Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies
- Lucía Campos-Prieto,
- Aitor García-Rey,
- Eddy Sotelo and
- Ana Mallo-Abreu
Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261
Graphical Abstract
Figure 1: Classical MCRs.
Figure 2: Different scaffolds that can be formed with the Ugi adduct.
Scheme 1: Oxoindole-β-lactam core produced in a U4C-3CR.
Figure 3: Most active oxoindole-β-lactam compounds developed by Brãndao et al. [33].
Scheme 2: Ugi-azide synthesis of benzofuran, pyrazole and tetrazole hybrids.
Figure 4: The most promising hybrids synthesized via the Ugi-azide multicomponent reaction reported by Kushwa...
Scheme 3: Four-component Ugi reaction for the synthesis of novel antioxidant compounds.
Figure 5: Most potent antioxidant compounds obtained through the Ugi four-component reaction developed by Pac...
Scheme 4: Four-component Ugi reaction to synthesize β-amiloyd aggregation inhibitors.
Figure 6: The most potential β-amiloyd aggregation inhibitors generated by Galante et al. [37].
Scheme 5: Four-component Ugi reaction to obtain FATH hybrids and the best candidate synthesized.
Scheme 6: Four-component Ugi reaction for the synthesis of FATMH hybrids and the best candidate synthesized.
Scheme 7: Petasis multicomponent reaction to produce pyrazine-based MTDLs.
Figure 7: Best pyrazine-based MTDLs synthesized by Madhav et al. [40].
Scheme 8: Synthesis of BCPOs employing a Knoevenagel-based multicomponent reaction and the best candidate syn...
Scheme 9: Hantzsch multicomponent reaction for the synthesis of DHPs as novel MTDLs.
Figure 8: Most active 1,4-dihydropyridines developed by Malek et al. [43].
Scheme 10: Chromone–donepezil hybrid MTDLs obtained via the Passerini reaction.
Figure 9: Best CDH-based MTDLs as AChE inhibitors synthesized by Malek et al. [46].
Scheme 11: Replacement of the nitrogen in lactams 11 with an oxygen in 12 to influence hydrogen-bond donating ...
Scheme 12: MCR 3 + 2 reaction to develop spirooxindole, spiroacenaphthylene, and bisbenzo[b]pyran compounds.
Figure 10: SIRT2 activity of best derivatives obtained by Hasaninejad et al. [49].
Scheme 13: Synthesis of ML192 analogs using the Gewald multicomponent reaction and the best candidate synthesi...
Scheme 14: Development of 1,5-benzodiazepines via Ugi/deprotection/cyclization (UDC) approach by Xu et al. [59].
Scheme 15: Synthesis of polysubstituted 1,4-benzodiazepin-3-ones using UDC strategy.
Scheme 16: Synthetic procedure to obtain 3-carboxamide-1,4-benzodiazepin-5-ones employing Ugi–reduction–cycliz...
Scheme 17: Ugi cross-coupling (U-4CRs) to synthesize triazolobenzodiazepines.
Scheme 18: Azido-Ugi four component reaction cyclization to obtain imidazotetrazolodiazepinones.
Scheme 19: Synthesis of oxazolo- and thiazolo[1,4]benzodiazepine-2,5-diones via Ugi/deprotection/cyclization a...
Scheme 20: General synthesis of 2,3-dichlorophenylpiperazine-derived compounds by the Ugi reaction and Ugi/dep...
Figure 11: Best DRD2 compounds synthesized using a multicomponent strategy.
Scheme 21: Bucherer–Bergs multicomponent reaction to obtain a key intermediate in the synthesis of pomaglumeta...
Scheme 22: Ugi reaction to synthesize racetam derivatives and example of two racetams synthesized by Cioc et a...
Hypervalent iodine-mediated intramolecular alkene halocyclisation
- Charu Bansal,
- Oliver Ruggles,
- Albert C. Rowett and
- Alastair J. J. Lennox
Beilstein J. Org. Chem. 2024, 20, 3113–3133, doi:10.3762/bjoc.20.258
Graphical Abstract
Figure 1: Example bioactive compounds containing cyclic scaffolds potentially accessible by HVI chemistry.
Figure 2: A general mechanism for HVI-mediated endo- or exo-halocyclisation.
Scheme 1: Metal-free synthesis of β-fluorinated piperidines 6. Ts = tosyl.
Scheme 2: Intramolecular aminofluorination of unactivated alkenes with a palladium catalyst.
Scheme 3: Aminofluorination of alkenes in the synthesis of enantiomerically pure β-fluorinated piperidines. P...
Scheme 4: Synthesis of β-fluorinated piperidines.
Scheme 5: Intramolecular fluoroaminations of unsaturated amines published by Li.
Scheme 6: Intramolecular aminofluorination of unsaturated amines using 1-fluoro-3,3-dimethylbenziodoxole (12)...
Scheme 7: 3-fluoropyrrolidine synthesis. aDiastereomeric ratio (cis/trans) determined by 19F NMR analysis.
Scheme 8: Kitamura’s synthesis of 3-fluoropyrrolidines. Values in parentheses represent the cis:trans ratio.
Scheme 9: Jacobsen’s enantio- and diastereoselective protocol for the synthesis of syn-β-fluoroaziridines 15.
Scheme 10: Different HVI reagents lead to different diastereoselectivity in aminofluorination competing with c...
Scheme 11: Fluorocyclisation of unsaturated alcohols and carboxylic acids to make tetrahydrofurans, fluorometh...
Scheme 12: Oxyfluorination of unsaturated alcohols.
Scheme 13: Synthesis and mechanism of fluoro-benzoxazepines.
Scheme 14: Intramolecular fluorocyclisation of unsaturated carboxylic acids. Yield of isolated product within ...
Scheme 15: Synthesis of fluorinated tetrahydrofurans and butyrolactone.
Scheme 16: Synthesis of fluorinated oxazolines 32. aReaction time increased to 40 hours. Yields refer to isola...
Scheme 17: Electrochemical synthesis of fluorinated oxazolines.
Scheme 18: Electrochemical synthesis of chromanes.
Scheme 19: Synthesis of fluorinated oxazepanes.
Scheme 20: Enantioselective oxy-fluorination with a chiral aryliodide catayst.
Scheme 21: Catalytic synthesis of 5‑fluoro-2-aryloxazolines using BF3·Et2O as a source of fluoride and an acti...
Scheme 22: Intramolecular carbofluorination of alkenes.
Scheme 23: Intramolecular chlorocyclisation of unsaturated amines.
Scheme 24: Synthesis of chlorinated cyclic guanidines 44.
Scheme 25: Synthesis of chlorinated pyrido[2,3-b]indoles 46.
Scheme 26: Chlorolactonization and chloroetherification reactions.
Scheme 27: Proposed mechanism for the synthesis of chloromethyl oxazolines 49.
Scheme 28: Oxychlorination to form oxazine and oxazoline heterocycles promoted by BCl3.
Scheme 29: Aminobromocyclisation of homoallylic sulfonamides 53. The cis:trans ratios based on the 1H NMR of t...
Scheme 30: Synthesis of cyclic imines 45.
Scheme 31: Synthesis of brominated pyrrolo[2,3-b]indoles 59.
Scheme 32: Bromoamidation of alkenes.
Scheme 33: Synthesis of brominated cyclic guanidines 61 and 61’.
Scheme 34: Intramolecular bromocyclisation of N-oxyureas.
Scheme 35: The formation of 3-bromoindoles.
Scheme 36: Bromolactonisation of unsaturated acids 68.
Scheme 37: Synthesis of 5-bromomethyl-2-oxazolines.
Scheme 38: Synthesis of brominated chiral morpholines.
Scheme 39: Bromoenolcyclisation of unsaturated dicarbonyl groups.
Scheme 40: Brominated oxazines and oxazolines with BBr3.
Scheme 41: Synthesis of 5-bromomethtyl-2-phenylthiazoline.
Scheme 42: Intramolecular iodoamination of unsaturated amines.
Scheme 43: Formation of 3-iodoindoles.
Scheme 44: Iodoetherification of 2,2-diphenyl-4-penten-1-carboxylic acid (47’) and 2,2-diphenyl-4-penten-1-ol (...
Scheme 45: Synthesis of 5-iodomethyl-2-oxazolines.
Scheme 46: Synthesis of chiral iodinated morpholines. aFrom the ʟ-form of the amino acid starting material. Th...
Scheme 47: Iodoenolcyclisation of unsaturated dicarbonyl compounds 74.
Scheme 48: Synthesis of 5-iodomethtyl-2-phenylthiazoline (87).
Giese-type alkylation of dehydroalanine derivatives via silane-mediated alkyl bromide activation
- Perry van der Heide,
- Michele Retini,
- Fabiola Fanini,
- Giovanni Piersanti,
- Francesco Secci,
- Daniele Mazzarella,
- Timothy Noël and
- Alberto Luridiana
Beilstein J. Org. Chem. 2024, 20, 3274–3280, doi:10.3762/bjoc.20.271
Graphical Abstract
Figure 1: Giese reaction: Radical addition on olefins with an electron-withdrawing group (EWG) followed by a ...
Figure 2: Alkyl bromide and Dha derivative scope. Reaction conditions: Dha derivative (0.5 mmol), alkyl bromi...
Figure 3: Scaled-up reaction. Reaction conditions: Dha derivative (2.2 mmol), alkyl bromide (5.4 mmol), tris(...
Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling
- John M. Halford-McGuff,
- Thomas M. Richardson,
- Aidan P. McKay,
- Frederik Peschke,
- Glenn A. Burley and
- Allan J. B. Watson
Beilstein J. Org. Chem. 2024, 20, 3198–3204, doi:10.3762/bjoc.20.265
Graphical Abstract
Scheme 1: The CuAAC reaction and installation of functional groups for product diversification.
Scheme 2: Scope of germanyl acetylene CuAAC. Alkyne (1.0 equiv), azide (1.1 equiv), CuSO4·5H2O (5.0 mol %), N...
Scheme 3: (a) Application of Ge-alkyne CuAAC to functional molecules. (b) Functionalisation of germylated tri...
Non-covalent organocatalyzed enantioselective cyclization reactions of α,β-unsaturated imines
- Sergio Torres-Oya and
- Mercedes Zurro
Beilstein J. Org. Chem. 2024, 20, 3221–3255, doi:10.3762/bjoc.20.268
Graphical Abstract
Figure 1: Reactivity of α,β-unsaturated imines and variety of structures.
Figure 2: The hetero-Diels–Alder and inverse electron demand hetero-Diels–Alder reactions.
Figure 3: Different strategies to promote the activation of dienes and dienophiles in IEDADA reactions.
Figure 4: Examples of non-covalent interactions in organocatalysis.
Scheme 1: Enantioselective bifunctional thiourea-catalyzed inverse electron demand Diels–Alder reaction of N-...
Scheme 2: Cinchona-derived thiourea-catalyzed stereoselective (3 + 2) reaction of α,β-unsaturated imines and ...
Scheme 3: Cinchona-derived thiourea-catalyzed stereoselective (3 + 2)/(4 + 2) cascade reaction of α,β-unsatur...
Scheme 4: Enantioselective bifunctional squaramide-catalyzed formal [4 + 2] cycloaddition of malononitrile wi...
Scheme 5: Bifunctional squaramide-catalyzed IEDADA reaction of saccharin-derived 1-azadienes and azlactones.
Scheme 6: Chiral guanidine-catalyzed enantioselective (4+1) cyclization of benzofuran-derived azadienes with ...
Scheme 7: Bifunctional squaramide-catalyzed [4 + 2] cyclization of benzofuran-derived azadienes and azlactone...
Scheme 8: Chiral bifunctional squaramide-catalyzed domino Mannich/formal [4 + 2] cyclization of 2-benzothiazo...
Scheme 9: Chiral bifunctional thiourea-catalyzed formal IEDADA reaction of β,γ-unsaturated ketones and benzof...
Scheme 10: Dihydroquinine-derived squaramide-catalyzed (3 + 2) cycloaddition reaction of isocyanoacetates and ...
Scheme 11: Enantioselective squaramide-catalyzed asymmetric IEDADA reaction of benzofuran-derived azadienes an...
Scheme 12: Scale up and derivatizations of benzofuran-fused 2-piperidinol derivatives.
Scheme 13: Dihydroquinine-derived squaramide-catalyzed Mannich-type reaction of isocyanoacetates with N-(2-ben...
Figure 5: Structure of a cinchona alkaloid and (DHQD)2PHAL.
Scheme 14: Enantioselective modified cinchona alkaloid-catalyzed [4 + 2] annulation of γ-butenolides and sacch...
Scheme 15: Chiral tertiary amine-catalyzed [2 + 4] annulation of cyclic 1-azadiene with γ-nitro ketones.
Scheme 16: Inverse electron demand aza-Diels–Alder reaction (IEDADA) of 1-azadienes with enecarbamates catalyz...
Scheme 17: Phosphoric acid-catalyzed enantioselective [4 + 2] cycloaddition of benzothiazolimines and enecarba...
Scheme 18: Phosphoric acid-catalyzed enantioselective inverse electron demand aza-Diels–Alder reaction of in s...
Scheme 19: Proposed reaction mechanism for the phosphoric acid-catalyzed enantioselective inverse electron dem...
Scheme 20: Enantioselective dearomatization of indoles by a (3 + 2) cyclization with azoalkenes catalyzed by a...
Scheme 21: Synthetic applicability of the pyrroloindoline derivatives.
Scheme 22: Chiral phosphoric acid-catalyzed (2 + 3) dearomative cycloaddition of 3-alkyl-2-vinylindoles with a...
Scheme 23: Chiral phosphoric acid-catalyzed asymmetric [4 + 2] cycloaddition of aurone-derived 1-azadienes and...
Scheme 24: Phosphoric acid-catalyzed enantioselective formal [4 + 2] cycloaddition of dienecarbamates and 2-be...
Scheme 25: Chiral phosphoric acid-catalyzed asymmetric inverse electron demand aza-Diels–Alder reaction of 1,3...
Scheme 26: Chiral phosphoric acid-catalyzed asymmetric Attanasi reaction between 1,3-dicarbonyl compounds and ...
Scheme 27: Synthetic applicability of the NPNOL derivatives.
Scheme 28: Chiral phosphoric acid-catalyzed asymmetric intermolecular formal (3 + 2) cycloaddition of azoalken...
Scheme 29: Enantioselective [4 + 2] cyclization of α,β-unsaturated imines and azlactones.
Scheme 30: Catalytic cycle for the chiral phosphoric acid-catalyzed enantioselective [4 + 2] cyclization of α,...
Synthetic applications of the Cannizzaro reaction
- Bhaskar Chatterjee,
- Dhananjoy Mondal and
- Smritilekha Bera
Beilstein J. Org. Chem. 2024, 20, 1376–1395, doi:10.3762/bjoc.20.120
Graphical Abstract
Figure 1: Types and mechanism of the Cannizzaro reaction.
Figure 2: Various approaches of the Cannizzaro reaction.
Figure 3: Representative molecules synthesized via the Cannizzaro reaction.
Scheme 1: Intramolecular Cannizzaro reaction of aryl glyoxal hydrates using TOX catalysts.
Scheme 2: Intramolecular Cannizzaro reaction of aryl methyl ketones using ytterbium triflate/selenium dioxide....
Scheme 3: Intramolecular Cannizzaro reaction of aryl glyoxals using Cr(ClO4)3 as catalyst.
Scheme 4: Cu(II)-PhBox-catalyzed asymmetric Cannizzaro reaction.
Scheme 5: FeCl3-based chiral catalyst applied for the enantioselective intramolecular Cannizzaro reaction rep...
Scheme 6: Copper bis-oxazoline-catalysed intramolecular Cannizzaro reaction and proposed mechanism.
Scheme 7: Chiral Fe catalysts-mediated enantioselective Cannizzaro reaction.
Scheme 8: Ruthenium-catalyzed Cannizzaro reaction of aromatic aldehydes.
Scheme 9: MgBr2·Et2O-assisted Cannizzaro reaction of aldehydes.
Scheme 10: LiBr-catalyzed intermolecular Cannizzaro reaction of aldehydes.
Scheme 11: γ-Alumina as a catalyst in the Cannizzaro reaction.
Scheme 12: AlCl3-mediated Cannizzaro disproportionation of aldehydes.
Scheme 13: Ru–N-heterocyclic carbene catalyzed dehydrogenative synthesis of carboxylic acids.
Figure 4: Proposed catalytic cycle for the dehydrogenation of alcohols.
Scheme 14: Intramolecular desymmetrization of tetraethylene glycol.
Scheme 15: Desymmetrization of oligoethylene glycol dialdehydes.
Scheme 16: Intramolecular Cannizzaro reaction of calix[4]arene dialdehydes.
Scheme 17: Desymmetrization of dialdehydes of symmetrical crown ethers using Ba(OH)2.
Scheme 18: Synthesis of ottelione A (proposed) via intramolecular Cannizzaro reaction.
Scheme 19: Intramolecular Cannizzaro reaction for the synthesis of pestalalactone.
Scheme 20: Synthetic strategy towards nigricanin involving an intramolecular Cannizzaro reaction.
Scheme 21: Spiro-β-lactone-γ-lactam part of oxazolomycins via aldol crossed-Cannizzaro reaction.
Scheme 22: Synthesis of indole alkaloids via aldol crossed-Cannizzaro reaction.
Scheme 23: Aldol and crossed-Cannizzaro reaction towards the synthesis of ertuliflozin.
Scheme 24: Synthesis of cyclooctadieneones using a Cannizzaro reaction.
Scheme 25: Microwave-assisted crossed-Cannizzaro reaction for the synthesis of 3,3-disubstituted oxindoles.
Scheme 26: Synthesis of porphyrin-based rings using the Cannizzaro reaction.
Scheme 27: Synthesis of phthalides and pestalalactone via Cannizarro–Tishchenko-type reaction.
Scheme 28: Synthesis of dibenzoheptalene bislactones via a double intramolecular Cannizzaro reaction.
Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts
- Mandeep K. Chahal
Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257
Graphical Abstract
Figure 1: Chemical structures of the main tetrapyrrolic macrocycles studied in this review for their role as ...
Figure 2: Calix[4]pyrroles 3 and 4 and an their acyclic analogue 5 used for the transformation of Danishefsky...
Figure 3: Calixpyrrole-based organocatalysts 11 and 12 for the diastereoselective addition reaction of TMSOF ...
Figure 4: (a) Chemical structures of macrocyclic organocatalysts used for the synthesis of cyclic carbonates ...
Figure 5: Cuprous chloride-catalyzed aziridination of styrene (22) by chloramine-T (23) providing 1-tosyl-2-p...
Figure 6: Chemical structures of the various porphyrin macrocycles (18, 25–41) screened as potential catalyst...
Figure 7: Organocatalytic activity of distorted porphyrins explored by Senge and co-workers. Planar macrocycl...
Figure 8: Chemical structures of H2EtxTPP (x = 0, 2, 4, 6, 8) compounds with incrementally increasing nonplan...
Figure 9: Chemical structures of OxP macrocycles tested as potential organocatalysts for the conjugate additi...
Figure 10: a) Fundamental structure of the J-aggregates of diprotonated TPPS3 53 and b) its use as a catalyst ...
Figure 11: Chemical structures of amphiphilic porphyrin macrocycles used as pH-switchable catalysts based on i...
Figure 12: a) Chemical structures of porphyrin macrocycles for the cycloaddition of CO2 to N-alkyl/arylaziridi...
Figure 13: Electron and energy-transfer processes typical for excited porphyrin molecules (Por = porphyrin mac...
Figure 14: Proposed mechanism for the light-induced α-alkylation of aldehydes with EDA in the presence of H2TP...
Figure 15: a) Chemical structures of porphyrins screened as photoredox catalysts, b) model reaction of furan (...
Figure 16: Porphyrin macrocycles H2TPP (18) and PPIX 78 as photoreductants for the red light-induced C–H aryla...
Figure 17: Porphyrin macrocycles H2TPP (18) and PPIX 78 as photoredox catalyst for (a) α-alkylation of an alde...
Figure 18: Corrole macrocycles 98–100 as photoredox catalysts for C–H arylation and borylation reactions. Adap...
Figure 19: Proposed catalytic cycle of electrocatalytic generation of H2 evolution using tetrapyrrolic macrocy...
Figure 20: a) Chemical structures of tetrapyrrolic macrocycles 109, 73, and 110 used for oxygen reductions in ...
Figure 21: a) Absorption spectra (left) of the air-saturated DCE solutions containing: 5 × 10−5 M H2TPP (black...
Figure 22: Chemical structures of N,N’-dimethylated saddle-distorted porphyrin isomers, syn-Me2P 111 and anti-...
Figure 23: Reaction mechanisms for the two-electron reduction of O2 by a) syn-Me2Iph 113 and b) anti-Me2Iph 114...
Figure 24: O2/H2O2 interconversion using methylated saddle-distorted porphyrin and isophlorin (reduced porphyr...
Figure 25: Chemical structures of distorted dodecaphenylporphyrin macrocycle 117 and its diprotonated form 118...
Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxide
- Noble Brako,
- Sreerag Moorkkannur Narayanan,
- Amber Burns,
- Layla Auter,
- Valentino Cesiliano,
- Rajeev Prabhakar and
- Norito Takenaka
Beilstein J. Org. Chem. 2024, 20, 3069–3076, doi:10.3762/bjoc.20.255
Graphical Abstract
Scheme 1: Metallotropic rearrangement and regioselectivity issues.
Scheme 2: Asymmetric catalytic allenylation of aldehydes.
Scheme 3: Selective preparation of propargyltrichlorosilane.
Scheme 4: Evaluation of C2-symmetric catalysts with benzaldehyde (1a) as a model aldehyde. Reaction condition...
Scheme 5: Evaluation of the extent to which (S)-8 catalyzed the allenylation reaction. Reaction conditions: a...
Figure 1: A potential energy surface (PES) for the proposed mechanism for (a) isomerization of propargyltrich...
A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis
- Magnus Rueping and
- Boris J. Nachtsheim
Beilstein J. Org. Chem. 2010, 6, No. 6, doi:10.3762/bjoc.6.6
Graphical Abstract
Scheme 1: AlCl3-mediated reaction between amyl chloride and benzene as developed by Friedel and Crafts.
Figure 1: Most often used metal salts for catalytic FC alkylations and hydroarylations of arenes.
Figure 2: 1,1-diarylalkanes with biological activity.
Scheme 2: Alkylating reagents and side products produced.
Scheme 3: Initially reported TeCl4-mediated FC alkylation of 1-penylethanol with toluene.
Scheme 4: Sc(OTf)3-catalyzed FC benzylation of arenes.
Scheme 5: Reductive FC alkylation of arenes with arenecarbaldehydes.
Scheme 6: Iron(III)-catalyzed FC benzylation of arenes and heteroarenes.
Scheme 7: A gold(III)-catalyzed route to beclobrate.
Scheme 8: Catalytic FC-type alkylations of 1,3-dicarbonyl compounds.
Scheme 9: Iron(III)-catalyzed synthesis of phenprocoumon.
Scheme 10: Bi(OTf)3-catalyzed FC alkylation of benzyl alcohols developed by Rueping et al.
Scheme 11: (A) Bi(OTf)3-catalyzed intramolecular FC alkylation as an efficient route to substituted fulvenes. ...
Scheme 12: FC-type glycosylation of 1,2-dimethylindole and trimethoxybenzene.
Scheme 13: FC alkylation with highly reactive ferrocenyl- and benzyl alcohols. The reaction proceeds even with...
Scheme 14: Reductive FC alkylation of arenes with benzaldehyde and acetophenone catalyzed by the Ir-carbene co...
Scheme 15: Formal synthesis of 1,1-diarylalkanes from benzyl alcohols and styrenes.
Scheme 16: (A) Mo-catalyzed hydroarylation of styrenes and cyclohexenes. (B) Hydroalkylation–cyclization casca...
Scheme 17: Bi(III)-catalyzed hydroarylation of styrenes with arenes and heteroarenes.
Scheme 18: BiCl3-catalyzed ene/FC alkylation reaction cascade – A fast access to highly arylated dihydroindene...
Scheme 19: Au(I)/Ag(I)-catalyzed hydroarylation of indoles with styrenes, aliphatic and cyclic alkenes.
Scheme 20: First transition-metal-catalyzed ortho-hydroarylation developed by Beller et al.
Scheme 21: (A) Ti(IV)-mediated rearrangement of an N-benzylated aniline to the corresponding ortho-alkylated a...
Scheme 22: Dibenzylation of aniline gives potentially useful amine-based ligands in a one-step procedure.
Scheme 23: FC-type alkylations with allyl alcohols as alkylating reagents – linear vs. branched product format...
Scheme 24: (A) First catalytic FC allylation and cinnamylation using allyl alcohols and its derivatives. (B) E...
Scheme 25: FC allylation/cyclization reaction yielding substituted chromanes.
Scheme 26: Synthesis of (all-rac)-α-tocopherol utilizing Lewis- and strong Brønsted-acids.
Scheme 27: Au(III)-catalyzed cinnamylation of arenes.
Scheme 28: “Exhaustive” allylation of benzene-1,3,5-triol.
Scheme 29: Palladium-catalyzed allylation of indole.
Scheme 30: Pd-catalyzed synthesis of pyrroloindoles from L-tryptophane.
Scheme 31: Ru(IV)-catalyzed allylation of indole and pyrroles with unique regioselectivity.
Scheme 32: Silver(I)-catalyzed intramolecular FC-type allylation of arenes and heteroarenes.
Scheme 33: FC-type alkylations of arenes using propargyl alcohols.
Scheme 34: (A) Propargylation of arenes with stoichiometric amounts of the Ru-allenylidene complex 86. (B) Fir...
Scheme 35: Diruthenium-catalyzed formation of chromenes and 1H-naphtho[2,1-b]pyrans.
Scheme 36: Rhenium(V)-catalyzed FC propargylations as a first step in the total synthesis of podophyllotoxin, ...
Scheme 37: Scandium-catalyzed arylation of 3-sulfanyl- and 3-selanylpropargyl alcohols.
Scheme 38: Synthesis of 1,3-diarylpropynes via direct coupling of propargyl trichloracetimidates and arenes.
Scheme 39: Diastereoselective substitutions of benzyl alcohols.
Scheme 40: (A) First diastereoselective FC alkylations developed by Bach et al. (B) anti-Selective FC alkylati...
Scheme 41: Diastereoselective AuCl3-catalyzed FC alkylation.
Scheme 42: Bi(OTf)3-catalyzed alkylation of α-chiral benzyl acetates with silyl enol ethers.
Scheme 43: Bi(OTf)3-catalyzed diastereoselective substitution of propargyl acetates.
Scheme 44: Nucelophilic substitution of enantioenriched ferrocenyl alcohols.
Scheme 45: First catalytic enantioselective propargylation of arenes.
