Search for "titanium dioxide" in Full Text gives 17 result(s) in Beilstein Journal of Organic Chemistry.
Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71
Graphical Abstract
Figure 1: Various pyrrole containing molecules.
Scheme 1: Various synthestic protocols for the synthesis of pyrroles.
Figure 2: A tree-diagram showing various conventional and green protocols for Clauson-Kaas pyrrole synthesis.
Scheme 2: A general reaction of Clauson–Kaas pyrrole synthesis and proposed mechanism.
Scheme 3: AcOH-catalyzed synthesis of pyrroles 5 and 7.
Scheme 4: Synthesis of N-substituted pyrroles 9.
Scheme 5: P2O5-catalyzed synthesis of N-substituted pyrroles 11.
Scheme 6: p-Chloropyridine hydrochloride-catalyzed synthesis of pyrroles 13.
Scheme 7: TfOH-catalyzed synthesis of N-sulfonylpyrroles 15, N-sulfonylindole 16, N-sulfonylcarbazole 17.
Scheme 8: Scandium triflate-catalyzed synthesis of N-substituted pyrroles 19.
Scheme 9: MgI2 etherate-catalyzed synthesis and proposed mechanism of N-arylpyrrole derivatives 21.
Scheme 10: Nicotinamide catalyzed synthesis of pyrroles 23.
Scheme 11: ZrOCl2∙8H2O catalyzed synthesis and proposed mechanism of pyrrole derivatives 25.
Scheme 12: AcONa catalyzed synthesis of N-substituted pyrroles 27.
Scheme 13: Squaric acid-catalyzed synthesis and proposed mechanism of N-substituted pyrroles 29.
Figure 3: Reusability of catalyst γ-Fe2O3@SiO2-Sb-IL in six cycles.
Scheme 14: Magnetic nanoparticle-supported antimony catalyst used in the synthesis of N-substituted pyrroles 31...
Scheme 15: Iron(III) chloride-catalyzed synthesis of N-substituted pyrroles 33.
Scheme 16: Copper-catalyzed Clauson–Kaas synthesis and mechanism of pyrroles 35.
Scheme 17: β-CD-SO3H-catalyzed synthesis and proposed mechanism of pyrroles 37.
Figure 4: Recyclability of β-cyclodextrin-SO3H.
Scheme 18: Solvent-free and catalyst-free synthesis and plausible mechanism of N-substituted pyrroles 39.
Scheme 19: Nano-sulfated TiO2-catalyzed synthesis of N-substituted pyrroles 41.
Figure 5: Plausible mechanism for the formation of N-substituted pyrroles catalyzed by nano-sulfated TiO2 cat...
Scheme 20: Copper nitrate-catalyzed Clauson–Kaas synthesis and mechanism of N-substituted pyrroles 43.
Scheme 21: Synthesis of N-substituted pyrroles 45 by using Co catalyst Co/NGr-C@SiO2-L.
Scheme 22: Zinc-catalyzed synthesis of N-arylpyrroles 47.
Scheme 23: Silica sulfuric acid-catalyzed synthesis of pyrrole derivatives 49.
Scheme 24: Bismuth nitrate-catalyzed synthesis of pyrroles 51.
Scheme 25: L-(+)-tartaric acid-choline chloride-catalyzed Clauson–Kaas synthesis and plausible mechanism of py...
Scheme 26: Microwave-assisted synthesis of N-substituted pyrroles 55 in AcOH or water.
Scheme 27: Synthesis of pyrrole derivatives 57 using a nano-organocatalyst.
Figure 6: Nano-ferric supported glutathione organocatalyst.
Scheme 28: Microwave-assisted synthesis of N-substituted pyrroles 59 in water.
Scheme 29: Iodine-catalyzed synthesis and proposed mechanism of pyrroles 61.
Scheme 30: H3PW12O40/SiO2-catalyzed synthesis of N-substituted pyrroles 63.
Scheme 31: Fe3O4@-γ-Fe2O3-SO3H-catalyzed synthesis of pyrroles 65.
Scheme 32: Mn(NO3)2·4H2O-catalyzed synthesis and proposed mechanism of pyrroles 67.
Scheme 33: p-TsOH∙H2O-catalyzed (method 1) and MW-assisted (method 2) synthesis of N-sulfonylpyrroles 69.
Scheme 34: ([hmim][HSO4]-catalyzed Clauson–Kaas synthesis of pyrroles 71.
Scheme 35: Synthesis of N-substituted pyrroles 73 using K-10 montmorillonite catalyst.
Scheme 36: CeCl3∙7H2O-catalyzed Clauson–Kaas synthesis of pyrroles 75.
Scheme 37: Synthesis of N-substituted pyrroles 77 using Bi(NO3)3∙5H2O.
Scheme 38: Oxone-catalyzed synthesis and proposed mechanism of N-substituted pyrroles 79.
Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126
Graphical Abstract
Scheme 1: Schematic overview of transition metals studied in C–H activation processes.
Scheme 2: (A) Known biological activities related to benzimidazole-based compounds; (B and C) an example of a...
Scheme 3: (A) Known biological activities related to quinoline-based compounds; (B and C) an example of a sca...
Scheme 4: (A) Known biological activities related to sulfur-containing compounds; (B and C) an example of a s...
Scheme 5: (A) Known biological activities related to aminoindane derivatives; (B and C) an example of a scand...
Scheme 6: (A) Known biological activities related to norbornane derivatives; (B and C) an example of a scandi...
Scheme 7: (A) Known biological activities related to aniline derivatives; (B and C) an example of a titanium-...
Scheme 8: (A) Known biological activities related to cyclohexylamine derivatives; (B) an example of an intram...
Scheme 9: (A) Known biologically active benzophenone derivatives; (B and C) photocatalytic oxidation of benzy...
Scheme 10: (A) Known bioactive fluorine-containing compounds; (B and C) vanadium-mediated C(sp3)–H fluorinatio...
Scheme 11: (A) Known biologically active Lythraceae alkaloids; (B) synthesis of (±)-decinine (30).
Scheme 12: (A) Synthesis of (R)- and (S)-boehmeriasin (31); (B) synthesis of phenanthroindolizidines by vanadi...
Scheme 13: (A) Known bioactive BINOL derivatives; (B and C) vanadium-mediated oxidative coupling of 2-naphthol...
Scheme 14: (A) Known antiplasmodial imidazopyridazines; (B) practical synthesis of 41.
Scheme 15: (A) Gold-catalyzed drug-release mechanism using 2-alkynylbenzamides; (B and C) chromium-mediated al...
Scheme 16: (A) Examples of anti-inflammatory benzaldehyde derivatives; (B and C) chromium-mediated difunctiona...
Scheme 17: (A and B) Manganese-catalyzed chemoselective intramolecular C(sp3)–H amination; (C) late-stage modi...
Scheme 18: (A and B) Manganese-catalyzed C(sp3)–H amination; (C) late-stage modification of a leelamine deriva...
Scheme 19: (A) Known bioactive compounds containing substituted N-heterocycles; (B and C) manganese-catalyzed ...
Scheme 20: (A) Known indoles that present GPR40 full agonist activity; (B and C) manganese-catalyzed C–H alkyl...
Scheme 21: (A) Examples of known biaryl-containing drugs; (B and C) manganese-catalyzed C–H arylation through ...
Scheme 22: (A) Known zidovudine derivatives with potent anti-HIV properties; (B and C) manganese-catalyzed C–H...
Scheme 23: (A and B) Manganese-catalyzed C–H organic photo-electrosynthesis; (C) late-stage modification.
Scheme 24: (A) Example of a known antibacterial silylated dendrimer; (B and C) manganese-catalyzed C–H silylat...
Scheme 25: (A and B) Fe-based small molecule catalyst applied for selective aliphatic C–H oxidations; (C) late...
Scheme 26: (A) Examples of naturally occurring gracilioethers; (B) the first total synthesis of gracilioether ...
Scheme 27: (A and B) Selective aliphatic C–H oxidation of amino acids; (C) late-stage modification of proline-...
Scheme 28: (A) Examples of Illicium sesquiterpenes; (B) first chemical synthesis of (+)-pseudoanisatin (80) in...
Scheme 29: (A and B) Fe-catalyzed deuteration; (C) late-stage modification of pharmaceuticals.
Scheme 30: (A and B) Biomimetic Fe-catalyzed aerobic oxidation of methylarenes to benzaldehydes (PMHS, polymet...
Scheme 31: (A) Known tetrahydroquinolines with potential biological activities; (B and C) redox-selective Fe c...
Scheme 32: (A) Known drugs containing a benzofuran unit; (B and C) Fe/Cu-catalyzed tandem O-arylation to acces...
Scheme 33: (A) Known azaindolines that act as M4 muscarinic acetylcholine receptor agonists; (B and C) intramo...
Scheme 34: (A) Known indolinones with anticholinesterase activity; (B and C) oxidative C(sp3)–H cross coupling...
Scheme 35: (A and B) Cobalt-catalyzed C–H alkenylation of C-3-peptide-containing indoles; (C) derivatization b...
Scheme 36: (A) Cobalt-Cp*-catalyzed C–H methylation of known drugs; (B and C) scope of the o-methylated deriva...
Scheme 37: (A) Known lasalocid A analogues; (B and C) three-component cobalt-catalyzed C–H bond addition; (D) ...
Scheme 38: (A and B) Cobalt-catalyzed C(sp2)–H amidation of thiostrepton.
Scheme 39: (A) Known 4H-benzo[d][1,3]oxazin-4-one derivatives with hypolipidemic activity; (B and C) cobalt-ca...
Scheme 40: (A and B) Cobalt-catalyzed C–H arylation of pyrrole derivatives; (C) application for the synthesis ...
Scheme 41: (A) Known 2-phenoxypyridine derivatives with potent herbicidal activity; (B and C) cobalt-catalyzed...
Scheme 42: (A) Natural cinnamic acid derivatives; (B and C) cobalt-catalyzed C–H carboxylation of terminal alk...
Scheme 43: (A and B) Cobalt-catalyzed C–H borylation; (C) application to the synthesis of flurbiprofen.
Scheme 44: (A) Benzothiazoles known to present anticonvulsant activities; (B and C) cobalt/ruthenium-catalyzed...
Scheme 45: (A and B) Cobalt-catalyzed oxygenation of methylene groups towards ketone synthesis; (C) synthesis ...
Scheme 46: (A) Known anticancer tetralone derivatives; (B and C) cobalt-catalyzed C–H difluoroalkylation of ar...
Scheme 47: (A and B) Cobalt-catalyzed C–H thiolation; (C) application in the synthesis of quetiapine (153).
Scheme 48: (A) Known benzoxazole derivatives with anticancer, antifungal, and antibacterial activities; (B and...
Scheme 49: (A and B) Cobalt-catalyzed C–H carbonylation of naphthylamides; (C) BET inhibitors 158 and 159 tota...
Scheme 50: (A) Known bioactive pyrrolo[1,2-a]quinoxalin-4(5H)-one derivatives; (B and C) cobalt-catalyzed C–H ...
Scheme 51: (A) Known antibacterial cyclic sulfonamides; (B and C) cobalt-catalyzed C–H amination of propargyli...
Scheme 52: (A and B) Cobalt-catalyzed intramolecular 1,5-C(sp3)–H amination; (C) late-stage functionalization ...
Scheme 53: (A and B) Cobalt-catalyzed C–H/C–H cross-coupling between benzamides and oximes; (C) late-state syn...
Scheme 54: (A) Known anticancer natural isoquinoline derivatives; (B and C) cobalt-catalyzed C(sp2)–H annulati...
Scheme 55: (A) Enantioselective intramolecular nickel-catalyzed C–H activation; (B) bioactive obtained motifs;...
Scheme 56: (A and B) Nickel-catalyzed α-C(sp3)–H arylation of ketones; (C) application of the method using kno...
Scheme 57: (A and B) Nickel-catalyzed C(sp3)–H acylation of pyrrolidine derivatives; (C) exploring the use of ...
Scheme 58: (A) Nickel-catalyzed C(sp3)–H arylation of dioxolane; (B) library of products obtained from biologi...
Scheme 59: (A) Intramolecular enantioselective nickel-catalyzed C–H cycloalkylation; (B) product examples, inc...
Scheme 60: (A and B) Nickel-catalyzed C–H deoxy-arylation of azole derivatives; (C) late-stage functionalizati...
Scheme 61: (A and B) Nickel-catalyzed decarbonylative C–H arylation of azole derivatives; (C) application of t...
Scheme 62: (A and B) Another important example of nickel-catalyzed C–H arylation of azole derivatives; (C) app...
Scheme 63: (A and B) Another notable example of a nickel-catalyzed C–H arylation of azole derivatives; (C) lat...
Scheme 64: (A and B) Nickel-based metalorganic framework (MOF-74-Ni)-catalyzed C–H arylation of azole derivati...
Scheme 65: (A) Known commercially available benzothiophene-based drugs; (B and C) nickel-catalyzed C–H arylati...
Scheme 66: (A) Known natural tetrahydrofuran-containing substances; (B and C) nickel-catalyzed photoredox C(sp3...
Scheme 67: (A and B) Another notable example of a nickel-catalyzed photoredox C(sp3)–H alkylation/arylation; (...
Scheme 68: (A) Electrochemical/nickel-catalyzed C–H alkoxylation; (B) achieved scope, including three using na...
Scheme 69: (A) Enantioselective photoredox/nickel catalyzed C(sp3)–H arylation; (B) achieved scope, including ...
Scheme 70: (A) Known commercially available trifluoromethylated drugs; (B and C) nickel-catalyzed C–H trifluor...
Scheme 71: (A and B) Stereoselective nickel-catalyzed C–H difluoroalkylation; (C) late-stage functionalization...
Scheme 72: (A) Cu-mediated ortho-amination of oxalamides; (B) achieved scope, including derivatives obtained f...
Scheme 73: (A) Electro-oxidative copper-mediated amination of 8-aminoquinoline-derived amides; (B) achieved sc...
Scheme 74: (A and B) Cu(I)-mediated C–H amination with oximes; (C) derivatization using telmisartan (241) as s...
Scheme 75: (A and B) Cu-mediated amination of aryl amides using ammonia; (C) late-stage modification of proben...
Scheme 76: (A and B) Synthesis of purine nucleoside analogues using copper-mediated C(sp2)–H activation.
Scheme 77: (A) Copper-mediated annulation of acrylamide; (B) achieved scope, including the synthesis of the co...
Scheme 78: (A) Known bioactive compounds containing a naphthyl aryl ether motif; (B and C) copper-mediated eth...
Scheme 79: (A and B) Cu-mediated alkylation of N-oxide-heteroarenes; (C) late-stage modification.
Scheme 80: (A) Cu-mediated cross-dehydrogenative coupling of polyfluoroarenes and alkanes; (B) scope from know...
Scheme 81: (A) Known anticancer acrylonitrile compounds; (B and C) Copper-mediated cyanation of unactivated al...
Scheme 82: (A) Cu-mediated radiofluorination of 8-aminoquinoline-derived aryl amides; (B) achieved scope, incl...
Scheme 83: (A) Examples of natural β-carbolines; (B and C) an example of a zinc-catalyzed C–H functionalizatio...
Scheme 84: (A) Examples of anticancer α-aminophosphonic acid derivatives; (B and C) an example of a zinc-catal...
Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125
Graphical Abstract
Figure 1: A) Bar chart of the publications per year for the topics “Photocatalysis” (49,662 instances) and “P...
Figure 2: A) Professor Giacomo Ciamician and Dr. Paolo Silber on their roof laboratory at the University of B...
Scheme 1: PRC trifluoromethylation of N-methylpyrrole (1) using hazardous gaseous CF3I safely in a flow react...
Figure 3: A) Unit cells of the three most common crystal structures of TiO2: rutile, brookite, and anatase. R...
Figure 4: Illustration of the key semiconductor photocatalysis events: 1) A photon with a frequency exceeding...
Figure 5: Photocatalytic splitting of water by oxygen vacancies on a TiO2(110) surface. Reprinted with permis...
Figure 6: Proposed adsorption modes of A) benzene, B) chlorobenzene, C) toluene, D) phenol, E) anisole, and F...
Figure 7: Structures of the sulfonate-containing organic dyes RB5 (3) and MX-5B (4) and the adsorption isothe...
Figure 8: Idealised triclinic unit cell of a g-C3N4 type polymer, displaying possible hopping transport scena...
Figure 9: Idealised structure of a perfect g-C3N4 sheet. The central unit highlighted in red represents one t...
Figure 10: Timeline of the key processes of charge transport following the photoexcitation of g-C3N4, leading ...
Scheme 2: Photocatalytic bifunctionalisation of heteroarenes using mpg-C3N4, with the selected examples 5 and ...
Figure 11: A) Structure of four linear conjugated polymer photocatalysts for hydrogen evolution, displaying th...
Figure 12: Graphical representation of the common methods used to immobilise molecular photocatalysts (PC) ont...
Figure 13: Wireless light emitter-supported TiO2 (TiO2@WLE) HPCat spheres powered by resonant inductive coupli...
Figure 14: Graphical representation of zinc–perylene diimide (Zn-PDI) supramolecular assembly photocatalysis v...
Scheme 3: Upconversion of NIR photons to the UV frequency by NaYF4:Yb,Tm nanocrystals sequentially coated wit...
Figure 15: Types of reactors employed in heterogeneous photocatalysis in flow. A) Fixed bed reactors and the s...
Figure 16: Electrochemical potential of common semiconductor, transition metal, and organic dye-based photocat...
Scheme 4: Possible mechanisms of an immobilised molecular photoredox catalyst by oxidative or reductive quenc...
Scheme 5: Scheme of the CMB-C3N4 photocatalytic decarboxylative fluorination of aryloxyacetic acids, with the...
Scheme 6: Scheme of the g-C3N4 photocatalytic desilylative coupling reaction in flow and proposed mechanism [208].
Scheme 7: Proposed mechanism of the radical cyclisation of unsaturated alkyl 2-bromo-1,3-dicarbonyl compounds...
Scheme 8: N-alkylation of benzylamine and schematic of the TiO2-coated microfluidic device [213].
Scheme 9: Proposed mechanism of the Pt@TiO2 photocatalytic deaminitive cyclisation of ʟ-lysine (23) to ʟ-pipe...
Scheme 10: A) Proposed mechanism for the photocatalytic oxidation of phenylboronic acid (24). B) Photos and SE...
Scheme 11: Proposed mechanism for the DA-CMP3 photocatalytic aza-Henry reaction performed in a continuous flow...
Scheme 12: Proposed mechanism for the formation of the cyclic product 32 by TiO2-NC HPCats in a slurry flow re...
Scheme 13: Reaction scheme for the photocatalytic synthesis of homo and hetero disulfides in flow and scope of...
Scheme 14: Reaction scheme for the MoOx/TiO2 HPCat oxidation of cyclohexane (34) to benzene. The graph shows t...
Scheme 15: Proposed mechanism of the TiO2 HPC heteroarene C–H functionalisation via aryl radicals generated fr...
Scheme 16: Scheme of the oxidative coupling of benzylamines with the HOTT-HATN HPCat and selected examples of ...
Scheme 17: Photocatalysis oxidation of benzyl alcohol (40) to benzaldehyde (41) in a microflow reactor coated ...
Figure 17: Mechanisms of Dexter and Forster energy transfer.
Scheme 18: Continuous flow process for the isomerisation of alkenes with an ionic liquid-immobilised photocata...
Scheme 19: Singlet oxygen synthetic step in the total synthesis of canataxpropellane [265].
Scheme 20: Scheme and proposed mechanism of the singlet oxygen photosensitisation by CMP_X HPCats, with the st...
Scheme 21: Structures of CMP HPCat materials applied by Vilela and co-workers for the singlet oxygen photosens...
Scheme 22: Polyvinylchloride resin-supported TDCPP photosensitisers applied for singlet oxygen photosensitisat...
Scheme 23: Structure of the ionically immobilised TPP photosensitiser on amberlyst-15 ion exchange resins (TPP...
Scheme 24: Photosensitised singlet oxygen oxidation of citronellol (46) in scCO2, with automatic phase separat...
Scheme 25: Schematic of PS-Est-BDP-Cl2 being applied for singlet oxygen photosensitisation in flow. A) Pseudo-...
Scheme 26: Reaction scheme of the singlet oxygen oxidation of furoic acid (54) using a 3D-printed microfluidic...
Figure 18: A) Photocatalytic bactericidal mechanism by ROS oxidative cleavage of membrane lipids (R = H, amino...
Figure 19: A) Suggested mechanisms for the aqueous pollutant degradation by TiO2 in a slurry flow reactor [284-287]. B)...
Figure 20: Schematic of the flow system used for the degradation of aqueous oxytetracycline (56) solutions [215]. M...
Scheme 27: Degradation of a salicylic acid (57) solution by a coupled solar photoelectro-Fenton (SPEF) process...
Figure 21: A) Schematic flow diagram using the TiO2-coated NETmix microfluidic device for an efficient mass tr...
Beilstein J. Org. Chem. 2018, 14, 2553–2567, doi:10.3762/bjoc.14.232
Graphical Abstract
Figure 1: (a) Structure and (b) reactivity of B12.
Figure 2: (a) Schematic representation of B12 enzyme-involving systems. (b) Construction of biomimetic and bi...
Scheme 1: (a) Carbon-skeleton rearrangement mediated by a coenzyme B12-depenedent enzyme. (b) Electrochemical...
Scheme 2: Electrochemical carbon-skeleton arrangements mediated by B12 model complexes.
Figure 3: Key electrochemical reactivity of 1 and 2 in methylated forms.
Scheme 3: Carbon-skeleton arrangements mediated by B12-vesicle artificial enzymes.
Scheme 4: Carbon-skeleton arrangements mediated by B12-HSA artificial enzymes.
Scheme 5: Photochemical carbon-skeleton arrangements mediated by B12-Ru@MOF.
Scheme 6: (a) Methyl transfer reaction mediated by B12-dependent methionine synthase. (b) Methyl transfer rea...
Scheme 7: Methyl transfer reaction for the detoxification of inorganic arsenics.
Scheme 8: (a) Dechlorination of 1,1,2,2-tetrarchloroethene mediated by a reductive dehalogenase. (b) Electroc...
Scheme 9: Visible-light-driven dechlorination of DDT using 1 in the presence of photosensitizers.
Scheme 10: 1,2-Migration of a phenyl group mediated by the visible-light-driven catalytic system composed of 1...
Scheme 11: Ring-expansion reactions mediated by the B12-TiO2 hybrid catalyst with UV-light irradiation.
Scheme 12: Trifluoromethylation and perfluoroalkylation of aromatic compounds achieved through electrolysis wi...
Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4
Graphical Abstract
Scheme 1: General overview over the sulfur-based substrates and reactive intermediates that are discussed in ...
Scheme 2: Photoredox-catalyzed radical thiol–ene reaction, applying [Ru(bpz)3](PF6)2 as photocatalyst.
Scheme 3: Photoredox-catalyzed thiol–ene reaction of aliphatic thiols with alkenes enabled by aniline derivat...
Scheme 4: Photoredox-catalyzed radical thiol–ene reaction for the postfunctionalization of polymers (a) and n...
Scheme 5: Photoredox-catalyzed thiol–ene reaction enabled by bromotrichloromethane as redox additive.
Scheme 6: Photoredox-catalyzed preparation of β-ketosulfoxides with Eosin Y as organic dye as photoredox cata...
Scheme 7: Greaney’s photocatalytic radical thiol–ene reaction, applying TiO2 nanoparticles as photocatalyst.
Scheme 8: Fadeyi’s photocatalytic radical thiol–ene reaction, applying Bi2O3 as photocatalyst.
Scheme 9: Ananikov’s photocatalytic radical thiol-yne reaction, applying Eosin Y as photocatalyst.
Scheme 10: Organocatalytic visible-light photoinitiated thiol–ene coupling, applying phenylglyoxylic acid as o...
Scheme 11: Xia’s photoredox-catalyzed synthesis of 2,3-disubstituted benzothiophenes, applying 9-mesityl-10-me...
Scheme 12: Wang’s metal-free photoredox-catalyzed radical thiol–ene reaction, applying 9-mesityl-10-methylacri...
Scheme 13: Visible-light benzophenone-catalyzed metal- and oxidant-free radical thiol–ene reaction.
Scheme 14: Visible-light catalyzed C-3 sulfenylation of indole derivatives using Rose Bengal as organic dye.
Scheme 15: Photocatalyzed radical thiol–ene reaction and subsequent aerobic sulfide-oxidation with Rose Bengal...
Scheme 16: Photoredox-catalyzed synthesis of diaryl sulfides.
Scheme 17: Photocatalytic cross-coupling of aryl thiols with aryl diazonium salts, using Eosin Y as photoredox...
Scheme 18: Photocatalyzed cross-coupling of aryl diazonium salts with cysteines in batch and in a microphotore...
Scheme 19: Fu’s [Ir]-catalyzed photoredox arylation of aryl thiols with aryl halides.
Scheme 20: Fu’s photoredox-catalyzed difluoromethylation of aryl thiols.
Scheme 21: C–S cross-coupling of thiols with aryl iodides via [Ir]-photoredox and [Ni]-dual-catalysis.
Scheme 22: C–S cross-coupling of thiols with aryl bromides, applying 3,7-bis-(biphenyl-4-yl)-10-(1-naphthyl)ph...
Scheme 23: Collin’s photochemical dual-catalytic cross-coupling of thiols with bromoalkynes.
Scheme 24: Visible-light-promoted C–S cross-coupling via intermolecular electron donor–acceptor complex format...
Scheme 25: Li’s visible-light photoredox-catalyzed thiocyanation of indole derivatives with Rose Bengal as pho...
Scheme 26: Hajra’s visible-light photoredox-catalyzed thiocyanation of imidazoheterocycles with Eosin Y as pho...
Scheme 27: Wang’s photoredox-catalyzed thiocyanation reaction of indoles, applying heterogeneous TiO2/MoS2 nan...
Scheme 28: Yadav’s photoredox-catalyzed α-C(sp3)–H thiocyanation reaction for tertiary amines, applying Eosin ...
Scheme 29: Yadav’s photoredox-catalyzed synthesis of 5-aryl-2-imino-1,3-oxathiolanes.
Scheme 30: Yadav’s photoredox-catalyzed synthesis of 1,3-oxathiolane-2-thiones.
Scheme 31: Li’s photoredox catalysis for the preparation of 2-substituted benzothiazoles, applying [Ru(bpy)3](...
Scheme 32: Lei’s external oxidant-free synthesis of 2-substituted benzothiazoles by merging photoredox and tra...
Scheme 33: Metal-free photocatalyzed synthesis of 2-aminobenzothiazoles, applying Eosin Y as photocatalyst.
Scheme 34: Metal-free photocatalyzed synthesis of 1,3,4-thiadiazoles, using Eosin Y as photocatalyst.
Scheme 35: Visible-light photoredox-catalyzed preparation of benzothiophenes with Eosin Y.
Scheme 36: Visible-light-induced KOH/DMSO superbase-promoted preparation of benzothiophenes.
Scheme 37: Jacobi von Wangelin’s photocatalytic approach for the synthesis of aryl sulfides, applying Eosin Y ...
Scheme 38: Visible-light photosensitized α-C(sp3)–H thiolation of aliphatic ethers.
Scheme 39: Visible-light photocatalyzed cross-coupling of alkyl and aryl thiosulfates with aryl diazonium salt...
Scheme 40: Visible-light photocatalyzed, controllable sulfenylation and sulfoxidation with organic thiosulfate...
Scheme 41: Rastogi’s photoredox-catalyzed methylsulfoxidation of aryl diazonium salts, using [Ru(bpy)3]Cl2 as ...
Scheme 42: a) Visible-light metal-free Eosin Y-catalyzed procedure for the preparation of vinyl sulfones from ...
Scheme 43: Visible-light photocatalyzed cross-coupling of sodium sulfinates with secondary enamides.
Scheme 44: Wang’s photocatalyzed oxidative cyclization of phenyl propiolates with sulfinic acids, applying Eos...
Scheme 45: Lei’s sacrificial oxidant-free synthesis of allyl sulfones by merging photoredox and transition met...
Scheme 46: Photocatalyzed Markovnikov-selective radical/radical cross-coupling of aryl sulfinic acids and term...
Scheme 47: Visible-light Eosin Y induced cross-coupling of aryl sulfinic acids and styrene derivatives, afford...
Scheme 48: Photoredox-catalyzed bicyclization of 1,7-enynes with sulfinic acids, applying Eosin Y as photocata...
Scheme 49: Visible-light-accelerated C–H-sulfinylation of arenes and heteroarenes.
Scheme 50: Visible-light photoredox-catalyzed β-selenosulfonylation of electron-rich olefins, applying [Ru(bpy)...
Scheme 51: Photocatalyzed preparation of β-chlorosulfones from the respective olefins and p-toluenesulfonyl ch...
Scheme 52: a) Photocatalyzed preparation of β-amidovinyl sulfones from sulfonyl chlorides. b) Preparation of β...
Scheme 53: Visible-light photocatalyzed sulfonylation of aliphatic tertiary amines, applying [Ru(bpy)3](PF6)2 ...
Scheme 54: Reiser’s visible-light photoredox-catalyzed preparation of β-hydroxysulfones from sulfonyl chloride...
Scheme 55: a) Sun’s visible-light-catalyzed approach for the preparation of isoquinolinonediones, applying [fac...
Scheme 56: Visible-light photocatalyzed sulfonylation/cyclization of vinyl azides, applying [Ru(bpy)3]Cl2 as p...
Scheme 57: Visible-light photocatalyzed procedure for the formation of β-ketosulfones from aryl sulfonyl chlor...
Scheme 58: Zheng’s method for the sulfenylation of indole derivatives, applying sulfonyl chlorides via visible...
Scheme 59: Cai’s visible-light induced synthesis of β-ketosulfones from sulfonyl hydrazines and alkynes.
Scheme 60: Photoredox-catalyzed approach for the preparation of vinyl sulfones from sulfonyl hydrazines and ci...
Scheme 61: Jacobi von Wangelin’s visible-light photocatalyzed chlorosulfonylation of anilines.
Scheme 62: Three-component photoredox-catalyzed synthesis of N-amino sulfonamides, applying PDI as organic dye....
Scheme 63: Visible-light induced preparation of complex sulfones from oximes, silyl enol ethers and SO2.
Beilstein J. Org. Chem. 2017, 13, 393–404, doi:10.3762/bjoc.13.42
Graphical Abstract
Figure 1: Adsorption of RNA on natural carbonate mineral samples.
Figure 2: Co-precipitation experiments on carbonate minerals for RNA-binding competition. The precipitated co...
Figure 3: RNA-induced calcium carbonate polymorphism. A: Feigl’s stain of CaCO3 precipitate formed by double ...
Figure 4: RNA adsorbed on aragonite is resistant to thermal degradation in aqueous solution. 18% denaturing P...
Beilstein J. Org. Chem. 2016, 12, 2873–2882, doi:10.3762/bjoc.12.286
Graphical Abstract
Figure 1: Adsorption of β-CD on the surface of nanoTiO2 [37].
Figure 2: Turbidity of nanoTiO2 dispersion (0.02%) in the presence of 1% HPBCD-P (green diamond) and 1% CMBCD...
Figure 3: Aggregation effect of 0.1% NaCl on 0.02% nanoTiO2 dispersion in the absence (green curve) and prese...
Figure 4: Aggregation effect of tap water on 0.02% nanoTiO2 dispersion in the absence (green curve) and prese...
Figure 5: Photodegradation of MB in aqueous solutions: distilled water (A), 0.1% NaCl solution (B) and tap wa...
Figure 6: Photodegradation of IBR in distilled water examining the drug itself (blue circle), and in the pres...
Beilstein J. Org. Chem. 2016, 12, 2358–2363, doi:10.3762/bjoc.12.229
Graphical Abstract
Figure 1: Rod mill, schematic (left) and photographs (middle and right).
Scheme 1: Oxidation of 4,4’-dimethoxybenzhydrol (1a) to 4,4’-dimethoxybenzophenone (1b).
Scheme 2: Scope for benzylic alcohol oxidation and obtained yields.
Scheme 3: Oxidation of 4-methoxyphenyl methyl carbinol (6a) to 4-methoxyacetophenone (6b).
Figure 2: 1H NMR (crude) of 4-methoxyacetophenone 6b.
Beilstein J. Org. Chem. 2015, 11, 1570–1582, doi:10.3762/bjoc.11.173
Graphical Abstract
Figure 1: Production and utilization of h+ and e– by photoactivation of a semiconductor.
Figure 2: Photoredox activity of TiO2 with moist air.
Scheme 1: TiO2 promoted oxidation of phenanthrene [29].
Scheme 2: SCPC assisted additions of allylic compounds to diazines and imines [40-42].
Scheme 3: TiO2 promoted addition and addition–cyclization reactions of tert-amines with electron-deficient al...
Scheme 4: Reactions of amines promoted by Pt-TiO2 [48,49].
Scheme 5: P25 Promoted alkylations of N-phenylmaleimide with diverse carboxylic acids [53,54]. aAccompanied by R–R d...
Scheme 6: SCPC cyclizations of aryloxyacetic acids with suitably sited alkene acceptors [54]. aYields in brackets...
Scheme 7: TiO2 promoted reactions of aryloxyacetic acids with maleic anhydride and maleimides [53,54].
Scheme 8: Photoredox addition–cyclization reactions of aryloxyacetic and related acids promoted by maleimide [63]....
Scheme 9: SCPC promoted homo-couplings and macrocyclizations with carboxylic acids [64].
Scheme 10: TiO2 promoted alkylations of alkenes with silanes [66] and thiols [67].
Scheme 11: TiO2 reduction of a nitrochromenone derivative [70].
Scheme 12: TiO2 mediated hydrodehalogenations and cyclizations of organic iodides [71].
Scheme 13: TiO2 promoted hydrogenations of maleimides, maleic anhydride and aromatic aldehydes [79].
Scheme 14: Mechanistic sketch of SCPC hydrogenation of aryl aldehydes.
Beilstein J. Org. Chem. 2015, 11, 828–836, doi:10.3762/bjoc.11.92
Graphical Abstract
Figure 1: A) A maximum rupture force (max force) histogram for a dopamine-functionalized tip is given for the...
Figure 2: A) Maximum force histograms for the different dwell times indicated in the inset normalized to the ...
Figure 3: Schematics of the different possibilities for attachment via multiple catechols. A) Multivalent att...
Figure 4: A) Force–distance curves where the rupture is not smooth but rather interrupted by a cluster of mea...
Beilstein J. Org. Chem. 2014, 10, 2765–2773, doi:10.3762/bjoc.10.293
Graphical Abstract
Figure 1: Proposed functional groups on purified DND surface.
Scheme 1: Overview on applied modification techniques to obtain DND with phosphate groups; conditions and rea...
Figure 2: ATR-FTIR spectra of species 3 and 6 from Scheme 1 in comparison to O-phosphorylethanolamine (O-PEA).
Figure 3: ATR-FTIR spectra of species involved in the synthesis process, from Scheme 1.
Figure 4: SEM images of titanium anodic oxide surface with: (a,b) unmodified DND; (c,d) DND-COOH functionaliz...
Figure 5: STEM image of immobilized aminosilanized DND 6 adsorbed to the air-formed passive layer of Ti6Al7Nb...
Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273
Graphical Abstract
Scheme 1: Principle of resistance mechanisms through selection of the most resistant micro-organism.
Figure 1: Chemical structure of carbendazim.
Scheme 2: Chemical structure of benomyl and its decomposition in aqueous solution.
Figure 2: Chemical structure of enilconazole.
Figure 3: Chemical structure of chloramidophos.
Scheme 3: The complex problem of pentachlorophenol (PCP) degradation.
Figure 4: Chemical structure of DCPE.
Figure 5: Chemical structures of some biocides used in [59].
Figure 6: Chemical structure of miconazole nitrate.
Figure 7: Chemical structures of triclosan and butylparaben.
Figure 8: Chemical structure of ciprofloxacin hydrochloride.
Figure 9: Chemical structure of benzethonium chloride.
Figure 10: Chemical structure of benzalkonium chlorides.
Scheme 4: Multiple equilibria of CD with benzalkonium chloride (BZK) and fluorometholone.
Scheme 5: Competition between co-micellization and biocidal activity observed for didecyldimethylammonium chl...
Scheme 6: Proposed antimicrobial mechanism of encapsulated didecyldimethylammonium chloride by CDs: (1) diffu...
Scheme 7: Inhibition of co-micellization process observed for didecyldimethylammonium chloride, octaethyleneg...
Scheme 8: Schematic representation of biocide release from a chemically cross-linked CD network.
Scheme 9: Proposed Trojan horse mechanism of silver nanoparticles capped by β-CD.
Scheme 10: Proposed mechanism of copper nanoparticles immobilized on carbon nanotube and embedded in water-ins...
Scheme 11: Advantages and drawback of the physicochemical and biopharmaceutical properties of CDs/biocides inc...
Beilstein J. Org. Chem. 2014, 10, 2556–2565, doi:10.3762/bjoc.10.267
Graphical Abstract
Figure 1: CO2 reduction to methanol in water promoted by FateDH, FaldDH and ADH where three consecutive 2e− s...
Figure 2: Transformed diffuse reflectance spectra of photocatalysts used in the present study.
Figure 3: a) Photoregeneration of 1,4-NADH using water as an electron donor: after 6 hours of irradiation of ...
Figure 4: 1H NMR spectra recorded at t = 0, after 2 and 6 h of irradiation in water. The selected range, 2–3 ...
Figure 5: 1H NMR spectrum of a standard 1,4-NADH (red line), and of 1,4-NADH formed from NAD+ upon photocatal...
Figure 6: Photocurrent generated at the [CrF5(H2O)]2−@TiO2 electrode as a function of the wavelength of the i...
Figure 7: Expected role of the rhodium complex as an electron mediator.
Figure 8: UV–vis absorption spectra of an aqueous solution of [Cp*Rh(bpy)(H2O)]2+. Continuous black line: spe...
Figure 9: Spectral changes of the [Cp*Rh(bpy)(H2O)]2+ solution as a function of the applied potential (left)....
Figure 10: Photoreduction of NAD+ as a function of concentration of glycerol (black line) and [Cp*Rh(bpy)H2O]Cl...
Figure 11: The electron flow in the photocatalytic system of NAD+ reduction composed of the photosensitized TiO...
Figure 12: Beads produced from Ca-alginate and TEOS containing co-encapsulated FateDH, FaldDH and ADH.
Figure 13: Assembled photocatalytic/enzymatic system for reduction of CO2 to CH3OH.
Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287
Graphical Abstract
Scheme 1: Pd-catalyzed monofluoromethylation of pinacol phenylboronate [44].
Scheme 2: Cu-catalyzed monofluoromethylation with 2-PySO2CHFCOR followed by desulfonylation [49].
Scheme 3: Cu-catalyzed difluoromethylation with α-silyldifluoroacetates [57].
Figure 1: Mechanism of the Cu-catalyzed C–CHF2 bond formation of α,β-unsaturated carboxylic acids through dec...
Scheme 4: Fe-catalyzed decarboxylative difluoromethylation of cinnamic acids [62].
Scheme 5: Preliminary experiments for investigation of the mechanism of the C–H trifluoromethylation of N-ary...
Figure 2: Plausible catalytic cycle proposed by Z.-J. Shi et al. for the trifluoromethylation of acetanilides ...
Figure 3: Plausible catalytic cycle proposed by M. S. Sanford et al. for the perfluoroalkylation of simple ar...
Figure 4: Postulated reaction pathway for the Ag/Cu-catalyzed trifluoromethylation of aryl iodides by Z. Q. W...
Figure 5: Postulated reaction mechanism for Cu-catalyzed trifluoromethylation reaction using MTFA as trifluor...
Scheme 6: Formal Heck-type trifluoromethylation of vinyl(het)arenes by M. Sodeoka et al. [83].
Figure 6: Proposed catalytic cycle for the copper-catalyzed trifluoromethylation of (het)arenes in presence o...
Figure 7: Proposed catalytic cycle for the copper-catalyzed trifluoromethylation of N,N-disubstituted (hetero...
Figure 8: Proposed catalytic cycle by Y. Zhang and J. Wang et al. for the copper-catalyzed trifluoromethylati...
Figure 9: Mechanistic rationale for the trifluoromethylation of arenes in presence of Langlois’s reagent and ...
Scheme 7: Trifluoromethylation of 4-acetylpyridine with Langlois’s reagent by P. S. Baran et al. (* Stirring ...
Scheme 8: Catalytic copper-facilitated perfluorobutylation of benzene with C4F9I and benzoyl peroxide [90].
Figure 10: F.-L. Qing et al.’s proposed mechanism for the copper-catalyzed trifluoromethylation of (hetero)are...
Figure 11: Mechanism of the Cu-catalyzed/Ru-photocatalyzed trifluoromethylation and perfluoroalkylation of ary...
Figure 12: Proposed mechanism for the Cu-catalyzed trifluoromethylation of aryl- and vinyl boronic acids with ...
Figure 13: Possible mechanism for the Cu-catalyzed decarboxylative trifluoromethylation of cinnamic acids [62].
Scheme 9: Ruthenium-catalyzed perfluoroalkylation of alkenes and (hetero)arenes with perfluoroalkylsulfonyl c...
Figure 14: N. Kamigata et al.’s proposed mechanism for the Ru-catalyzed perfluoroalkylation of alkenes and (he...
Figure 15: Proposed mechanism for the Ru-catalyzed photoredox trifluoromethylation of (hetero)arenes with trif...
Figure 16: Late-stage trifluoromethylation of pharmaceutically relevant molecules with trifluoromethanesulfony...
Figure 17: Proposed mechanism for the trifluoromethylation of alkenes with trifluoromethyl iodide under Ru-bas...
Scheme 10: Formal perfluoroakylation of terminal alkenes by Ru-catalyzed cross-metathesis with perfluoroalkyle...
Figure 18: One-pot Ir-catalyzed borylation/Cu-catalyzed trifluoromethylation of complex small molecules by Q. ...
Figure 19: Mechanistic proposal for the Ni-catalyzed perfluoroalkylation of arenes and heteroarenes with perfl...
Scheme 11: Electrochemical Ni-catalyzed perfluoroalkylation of 2-phenylpyridine (Y. H. Budnikova et al.) [71].
Scheme 12: Fe(II)-catalyzed trifluoromethylation of arenes and heteroarenes with trifluoromethyl iodide (T. Ya...
Figure 20: Mechanistic proposal by T. Yamakawa et al. for the Fe(II)-catalyzed trifluoromethylation of arenes ...
Scheme 13: Ytterbium-catalyzed perfluoroalkylation of dihydropyran with perfluoroalkyl iodide (Y. Ding et al.) ...
Figure 21: Mechanistic proposal by A. Togni et al. for the rhenium-catalyzed trifluoromethylation of arenes an...
Figure 22: Mechanism of the Cu-catalyzed oxidative trifluoromethylthiolation of arylboronic acids with TMSCF3 ...
Scheme 14: Removal of the 8-aminoquinoline auxiliary [136].
Figure 23: Mechanism of the Cu-catalyzed trifluoromethylthiolation of C–H bonds with a trifluoromethanesulfony...
Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265
Graphical Abstract
Scheme 1: Scaled industrial processes for the synthesis of simple pyridines.
Scheme 2: Synthesis of nicotinic acid from 2-methyl-5-ethylpyridine (1.11).
Scheme 3: Synthesis of 3-picoline and nicotinic acid.
Scheme 4: Synthesis of 3-picoline from 2-methylglutarodinitrile 1.19.
Scheme 5: Picoline-based synthesis of clarinex (no yields reported).
Scheme 6: Mode of action of proton-pump inhibitors and structures of the API’s.
Scheme 7: Hantzsch-like route towards the pyridine rings in common proton pump inhibitors.
Figure 1: Structures of rosiglitazone (1.40) and pioglitazone (1.41).
Scheme 8: Synthesis of rosiglitazone.
Scheme 9: Syntheses of 2-pyridones.
Scheme 10: Synthesis and mechanism of 2-pyrone from malic acid.
Scheme 11: Polymer-assisted synthesis of rosiglitazone.
Scheme 12: Synthesis of pioglitazone.
Scheme 13: Meerwein arylation reaction towards pioglitazone.
Scheme 14: Route towards pioglitazone utilising tyrosine.
Scheme 15: Route towards pioglitazone via Darzens ester formation.
Scheme 16: Syntheses of the thiazolidinedione moiety.
Scheme 17: Synthesis of etoricoxib utilising Negishi and Stille cross-coupling reactions.
Scheme 18: Synthesis of etoricoxib via vinamidinium condensation.
Figure 2: Structures of nalidixic acid, levofloxacin and moxifloxacin.
Scheme 19: Synthesis of moxifloxacin.
Scheme 20: Synthesis of (S,S)-2,8-diazabicyclo[4.3.0]nonane 1.105.
Scheme 21: Synthesis of levofloxacin.
Scheme 22: Alternative approach to the levofloxacin core 1.125.
Figure 3: Structures of nifedipine, amlodipine and clevidipine.
Scheme 23: Mg3N2-mediated synthesis of nifedipine.
Scheme 24: Synthesis of rac-amlodipine as besylate salt.
Scheme 25: Aza Diels–Alder approach towards amlodipine.
Scheme 26: Routes towards clevidipine.
Figure 4: Examples of piperidine containing drugs.
Figure 5: Discovery of tiagabine based on early leads.
Scheme 27: Synthetic sequences to tiagabine.
Figure 6: Structures of solifenacin (2.57) and muscarine (2.58).
Scheme 28: Enantioselective synthesis of solifenacin.
Figure 7: Structures of DPP-4 inhibitors of the gliptin-type.
Scheme 29: Formation of inactive diketopiperazines from cis-rotameric precursors.
Figure 8: Co-crystal structure of carmegliptin bound in the human DPP-4 active site (PDB 3kwf).
Scheme 30: Improved route to carmegliptin.
Figure 9: Structures of lamivudine and zidovudine.
Scheme 31: Typical routes accessing uracil, thymine and cytosine.
Scheme 32: Coupling between pyrimidones and riboses via the Vorbrüggen nucleosidation.
Scheme 33: Synthesis of lamivudine.
Scheme 34: Synthesis of raltegravir.
Scheme 35: Mechanistic studies on the formation of 3.22.
Figure 10: Structures of selected pyrimidine containing drugs.
Scheme 36: General preparation of pyrimidines and dihydropyrimidones.
Scheme 37: Synthesis of imatinib.
Scheme 38: Flow synthesis of imatinib.
Scheme 39: Syntheses of erlotinib.
Scheme 40: Synthesis of erlotinib proceeding via Dimroth rearrangement.
Scheme 41: Synthesis of lapatinib.
Scheme 42: Synthesis of rosuvastatin.
Scheme 43: Alternative preparation of the key aldehyde towards rosuvastatin.
Figure 11: Structure comparison between nicotinic acetylcholine receptor agonists.
Scheme 44: Syntheses of varenicline and its key building block 4.5.
Scheme 45: Synthetic access to eszopiclone and brimonidine via quinoxaline intermediates.
Figure 12: Bortezomib bound in an active site of the yeast 20S proteasome ([114], pdb 2F16).
Scheme 46: Asymmetric synthesis of bortezomib.
Figure 13: Structures of some prominent piperazine containing drugs.
Figure 14: Structural comparison between the core of aplaviroc (4.35) and a type-1 β-turn (4.36).
Scheme 47: Examplary synthesis of an aplaviroc analogue via the Ugi-MCR.
Scheme 48: Syntheses of azelastine (5.1).
Figure 15: Structures of captopril, enalapril and cilazapril.
Scheme 49: Synthesis of cilazapril.
Figure 16: Structures of lamotrigine, ceftriaxone and azapropazone.
Scheme 50: Synthesis of lamotrigine.
Scheme 51: Alternative synthesis of lamotrigine (no yields reported).
Figure 17: Structural comparison between imiquimod and the related adenosine nucleoside.
Scheme 52: Conventional synthesis of imiquimod (no yields reported).
Scheme 53: Synthesis of imiquimod.
Scheme 54: Synthesis of imiquimod via tetrazole formation (not all yields reported).
Figure 18: Structures of various anti HIV-medications.
Scheme 55: Synthesis of abacavir.
Figure 19: Structures of diazepam compared to modern replacements.
Scheme 56: Synthesis of ocinaplon.
Scheme 57: Access to zaleplon and indiplon.
Scheme 58: Different routes towards the required N-methylpyrazole 6.65 of sildenafil.
Scheme 59: Polymer-supported reagents in the synthesis of key aminopyrazole 6.72.
Scheme 60: Early synthetic route to sildenafil.
Scheme 61: Convergent preparations of sildenafil.
Figure 20: Comparison of the structures of sildenafil, tadalafil and vardenafil.
Scheme 62: Short route to imidazotriazinones.
Scheme 63: Alternative route towards vardenafils core imidazotriazinone (6.95).
Scheme 64: Bayer’s approach to the vardenafil core.
Scheme 65: Large scale synthesis of vardenafil.
Scheme 66: Mode of action of temozolomide (6.105) as methylating agent.
Scheme 67: Different routes to temozolomide.
Scheme 68: Safer route towards temozolomide.
Figure 21: Some unreported heterocyclic scaffolds in top market drugs.
Beilstein J. Org. Chem. 2012, 8, 2025–2052, doi:10.3762/bjoc.8.229
Graphical Abstract
Figure 1: An immersion-well batch reactor with 125 W medium pressure Hg lamp.
Figure 2: Transmission profile of a 0.05 M solution, ε = 200 M−1 cm−1.
Figure 3: Schematic of a typical microflow photochemical reactor (above) and detail of a triple-channel micro...
Figure 4: Schematic of a typical macroflow photochemical reactor (above) and images of the FEP photochemical ...
Scheme 1: [2 + 2] photocycloadditions of enones with enol derivatives.
Scheme 2: Competing reactions in an intramolecular [2 + 2] photocycloaddition.
Scheme 3: Diastereocontrolled cycloaddition of a cyclic enone with cyclopentene.
Scheme 4: Comparison of yields and reaction times for a batch reactor with a microflow system.
Scheme 5: Intramolecular [2 + 2] photocycloaddition.
Scheme 6: Paterno–Büchi reaction of benzophenone with an allylic alcohol.
Scheme 7: Photooxygenation of cyclopentadiene.
Scheme 8: Preparation of the anthelmintic ascaridole 23.
Scheme 9: Production of rose oxide 27 from (−)-β-citronellol (24).
Scheme 10: Photocatalytic alkylation of benzylamine.
Scheme 11: Photocatalytic reduction of 4-nitroacetophenone.
Scheme 12: Conversion of L-lysine to L-pipecolinic acid.
Scheme 13: Photocatalytic hydrodehalogenation.
Scheme 14: Photocatalytic aza-Henry reactions.
Scheme 15: Photocatalytic α-alkylation of aliphatic ketones.
Scheme 16: Decarboxylative photochemical additions.
Scheme 17: Photochemical addition of isopropanol to furanones.
Scheme 18: Photochemical addition of methanol to limonene.
Scheme 19: Light-promoted reduction of flavone.
Scheme 20: Photoreduction of benzophenone with benzhydrol.
Scheme 21: Barton reaction in a microflow system.
Scheme 22: Microflow synthesis of vitamin D3.
Scheme 23: photochemical chlorination of cyclohexane.
Scheme 24: photochemical cyanation of pyrene.
Scheme 25: Intermolecular [2 + 2] cycloaddition of maleimide (76) and intramolecular [2 + 2] cycloaddition of ...
Scheme 26: Intramolecular [5 + 2] cycloaddition of maleimide under flow conditions.
Scheme 27: Intramolecular [5 + 2] cycloaddition as a key step in the synthesis of (±)-neostenine.
Scheme 28: In situ generation of a thioaldehyde by photolysis of a phenacyl sulfide.
Scheme 29: Photodimerisation of maleic anhydride.
Scheme 30: [2 + 2] cycloaddition of a chiral enone with ethylene.
Scheme 31: Intramolecular [2 + 2] cycloaddition of a cyclopentenone.
Scheme 32: Photochemical Wolff rearrangement and cyclisation to β-lactams.
Scheme 33: Photochemical rearrangement of aryl azides.
Scheme 34: Rearrangement of quinoline N-oxides to quinolones.
Scheme 35: Photochemical rearrangement of cyclobutenones.
Scheme 36: Photoisomerisation en route to a vitamin-D derivative.
Scheme 37: Schematic of the Seeberger photooxygenation apparatus and sensitised photooxygenation of citronello...
Scheme 38: Sensitised photooxygenation of dihydroartemisinic acid.
Scheme 39: Photochemical preparation of CpRu(MeCN)3PF6.
Scheme 40: In situ photochemical generation and reaction of a [CpRu]+ catalyst.
Scheme 41: Intermolecular alkene–alkyne coupling with photogenerated catalyst.
Scheme 42: PET deoxygenation of nucleosides.
Scheme 43: Photochemical defluorination of DABFT.
Scheme 44: Aromatic azide reduction by visible-light-mediated photocatalysis.
Scheme 45: Examples of visible-light-mediated reactions.
Scheme 46: Visible-light-mediated formation of iminium ions.
Scheme 47: Examples of visible-light-mediated photocatalytic reactions.
Scheme 48: Anhydride formation from a visible-light-mediated process.
Scheme 49: Light-mediated conjugate addition of glycosyl bromide 141 to acrolein.
Scheme 50: Visible-light-mediated photocyclisation to [5]helicene.
Beilstein J. Org. Chem. 2009, 5, No. 24, doi:10.3762/bjoc.5.24
Graphical Abstract
Scheme 1: Titanium dioxide/TEMPO mediated synthesis of quinoxalines.