Recent advances of visible-light photocatalysis in the functionalization of organic compounds

Vishal Srivastava1, Pravin K. Singh1, Praveen P. Singh2
1Department of Chemistry, CMP Degree College, University of Allahabad, Prayagraj, 211002, India.
2Department of Chemistry, United College of Engineering & Research, Prayagraj 211010, India

Tài liệu tham khảo

Crisenza, 2020, Chemistry glows green with photoredox catalysis, Nat. Commun., 11, 803, 10.1038/s41467-019-13887-8 Kärkäs, 2016, Photochemical approaches to complex chemotypes: applications in natural product synthesis, Chem. Rev., 116, 9638, 10.1021/acs.chemrev.5b00760 Bach, 2011, Photochemical reactions as key steps in natural product synthesis, Angew. Chem. Int. Ed., 50, 1000, 10.1002/anie.201002845 Hoffmann, 2008, Photochemical reactions as key steps in organic synthesis, Chem. Rev., 108, 1052, 10.1021/cr0680336 Shaw, 2016, Photoredox catalysis in organic chemistry, J. Org. Chem., 81, 6898, 10.1021/acs.joc.6b01449 Narayanam, 2011, Visible light photoredox catalysis: applications in organic synthesis, Chem. Soc. Rev., 40, 102, 10.1039/B913880N Xuan, 2012, Visible-light photoredox catalysis, Angew. Chem. Int. Ed., 51, 6828, 10.1002/anie.201200223 Reckenthäler, 2013, Photoredox catalysis for organic syntheses, Adv. Synth. Catal., 355, 2727, 10.1002/adsc.201300751 Prier, 2013, Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis, Chem. Rev., 113, 5322, 10.1021/cr300503r Schultz, 2014, Solar synthesis: prospects in visible light photocatalysis, Science, 343, 10.1126/science.1239176 Zeitler, 2009, Photoredox catalysis with visible light, Angew. Chem., Int. Ed., 48, 9785, 10.1002/anie.200904056 Special issue, 2016, Photoredox catalysis in organic chemistry, Acc. Chem. Res., 49 Prier, 2013, Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis, Chem. Rev., 113, 5322, 10.1021/cr300503r Marzo, 2018, Visible-light photocatalysis: does it make a difference in organic synthesis?, Angew. Chem. Int. Ed., 57, 10034, 10.1002/anie.201709766 Chemical Photocatalysis; B. König, Ed.; deGruyter: Berlin, 2013. Visible Light Photocatalysis in Organic Chemistry; C. R. J. Stephenson, T. P. Yoon and D. W. C. MacMillan, Eds.; Wiley-VCH: Weinheim, 2018. Hopkinson, 2014, Dual catalysis sees the light: combining photoredox with organo, acid, and transition-metal catalysis, Chem. Eur. J., 20, 3874, 10.1002/chem.201304823 Skubi, 2016, Dual catalysis strategies in photochemical synthesis, Chem. Rev., 116, 10035, 10.1021/acs.chemrev.6b00018 DiRocco, 2014, Late-stage functionalization of biologically active heterocycles through photoredox catalysis, Angew. Chem. Int. Ed., 53, 4802, 10.1002/anie.201402023 Cernak, 2016, The medicinal chemist's toolbox for late stage functionalization of drug-like molecules, Chem. Soc. Rev., 45, 546, 10.1039/C5CS00628G Corrigan, 2016, Photocatalysis in organic and polymer synthesis, Chem. Soc. Rev., 45, 6165, 10.1039/C6CS00185H Michaudel, 2017, Cationic polymerization: from photoinitiation to photocontrol, Angew. Chem. Int. Ed., 56, 9670, 10.1002/anie.201701425 Chen, 2016, Light-controlled radical polymerization: mechanisms, methods, and applications, Chem. Rev., 116, 10167, 10.1021/acs.chemrev.5b00671 Mastandrea, 2021, Photoredox dual catalysis: a fertile playground for the discovery of new reactivities, Eur. J. Inorg. Chem., 10.1002/ejic.202100455 Capaldo, 2020, Photocatalytic hydrogen atom transfer: the philosopher's stone for late-stage functionalization?, Green Chem., 22, 3376, 10.1039/D0GC01035A Douglas, 2016, Visible light photocatalysis: applications and new disconnections in the synthesis of pharmaceutical agents, Org. Process. Res. Dev., 20, 1134, 10.1021/acs.oprd.6b00125 Li, 2020, Visible-light photocatalysis as an enabling technology for drug discovery: a paradigm shift for chemical reactivity, ACS Med. Chem. Lett., 11, 2120, 10.1021/acsmedchemlett.0c00436 Bogdos, 2018, Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry, Beilstein J. Org. Chem., 14, 2035, 10.3762/bjoc.14.179 Campos, 2019, The importance of synthetic chemistry in the pharmaceutical industry, Science, 363, eaat0805, 10.1126/science.aat0805 Sheldon, 2018, Metrics of green chemistry and sustainability: past, present, and future, ACS Sustain. Chem. Eng., 6, 32, 10.1021/acssuschemeng.7b03505 Schultz, 2020, Harder, better, faster, Nat. Chem., 12, 661, 10.1038/s41557-020-0510-8 Srivastava, 2014, Novel one-pot facile synthesis of thiopyranopyrazole using [H mim]HSO4 catalyst, Croat. Chem. Acta, 87, 91, 10.5562/cca2372 Srivastava, 2015, Eosin Y catalyzed visible-light-promoted one –pot facile synthesis of 1,3,4- thiadiazole, Croat. Chem. Acta, 88, 59, 10.5562/cca2520 Srivastava, 2015, Eosin Y catalysed visible light promoted aerobic oxidative cyclization of 2-aminobenzothiazole, Croat. Chem. Acta, 88, 227, 10.5562/cca2632 Srivastava, 2016, Trifluoromethylation of disubstituted morpholines by metal-free visible light photoredox catalysis, Asian J. Chem., 28, 2159, 10.14233/ajchem.2016.19893 Srivastava, 2016, [bmim]OH Catalyzed four component one-pot synthesis of imidazo[4,5-C]Pyrazole-2-Thione-N-Nucleosides, Rev. Roum. Chim., 61, 755 Srivastava, 2017, Visible light promoted allylic C–H oxidation, Croat. Chem. Acta, 90, 435, 10.5562/cca3126 Srivastava, 2017, Eosin Y catalyzed photoredox synthesis: a review, RSC Adv., 7, 31377, 10.1039/C7RA05444K Srivastava, 2018, Photoredox catalysed synthesis of amino alcohol, N. J. Chem., 42, 688, 10.1039/C7NJ03068A Singh, 2018, Facile aerobic photo-oxidative synthesis of sulfinic esters, Croat. Chem. Acta, 91, 383, 10.5562/cca3401 Srivastava, 2019, Visible light photoredox catalysed amidation of carboxylic acids with amines, Tetrahedron Lett., 60, 40, 10.1016/j.tetlet.2018.11.050 Srivastava, 2019, Photocatalysed eosin Y mediated C(sp3)-H alkylation of amine substrates via direct HAT, Tetrahedron Lett., 60, 1333, 10.1016/j.tetlet.2019.04.016 Srivastava, 2019, Eosin Y catalysed visible-light mediated aerobic oxidation of tertiary amines, Tetrahedron Lett., 60, 10.1016/j.tetlet.2019.151041 Srivastava, 2020, Recent application of visible-light induced radicals in C–S bond formation, RSC Adv., 10, 20046, 10.1039/D0RA03086D Srivastava, 2020, Visible light promoted synthesis of disubstituted 1,2,3-thiadiazoles, Rev. Roum. Chim., 65, 221, 10.33224/rrch.2020.65.3.01 Srivastava, 2020, Recent applications of rose bengal catalysis in N-heterocycles: a short review, RSC Adv., 10, 39495, 10.1039/D0RA07400D Srivastava, 2021, Synthetic applications of flavin photocatalysis: a review, RSC Adv., 11, 14251, 10.1039/D1RA00925G Srivastava, 2021, Recent advances of 4DPAIPN in photocatalytic transformations, Org. Biomol. Chem., 19, 313, 10.1039/D0OB01884H Singh, 2021, Recent applications of photoredox catalysis in O-heterocycles: a short review, Synth. Commun., 51, 3033, 10.1080/00397911.2021.1968907 Srivastava, 2021, Photochem, 1, 237, 10.3390/photochem1020014 Srivastava, 2022, Visible light photocatalysis in synthesis of pharmaceutically relevant heterocyclic scaffolds, Org. Chem. Front., 10.1039/D1QO01602D Prier, 2013, Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis, Chem. Rev., 113, 5322, 10.1021/cr300503r Pagire, 2020, Shining visible light on vinyl halides: expanding the horizons of photocatalysis, Acc. Chem. Res., 53, 782, 10.1021/acs.accounts.9b00615 Zhang, 2020, Titanocenes as photoredox catalysts using green-light irradiation, Angew. Chem. Int. Ed., 59, 9355, 10.1002/anie.202001508 Zidan, 2018, Recent advances in mono and binuclear gold photoredox catalysis, Catal. Sci. Technol., 8, 6019, 10.1039/C8CY01765D Zidan, 2020, Formal bromine atom transfer radical addition of nonactivated bromoalkanes using photoredox gold catalysis, Org. Lett., 22, 8401, 10.1021/acs.orglett.0c03030 Renneke, 1990, Polyoxometalate systems for the catalytic selective production of nonthermodynamic alkenes from alkanes. nature of excited-state deactivation processes and control of subsequent thermal processes in polyoxometalate photoredox chemistry, J. Am. Chem. Soc., 112, 6585, 10.1021/ja00174a020 Tzirakis, 2009, Decatungstate as an efficient photocatalyst in organic chemistry, Chem. Soc. Rev., 38, 2609, 10.1039/b812100c Yamase, 1984, Solution photochemistry of tetrakis(tetrabutylammonium) decatungstate(VI) and catalytic hydrogen evolution from alcohols, J. Chem. Soc. Dalton Trans., 793, 10.1039/dt9840000793 Montanaro, 2012, Decatungstate as photoredox catalyst: benzylation of electron-poor olefins, Org. Lett., 14, 4218, 10.1021/ol301900p Sarver, 2020, The merger of decatungstate and copper catalysis to enable aliphatic C(sp3)-H trifluoromethylation, Nat. Chem., 12, 459, 10.1038/s41557-020-0436-1 Romero, 2016, Organic photoredox catalysis, Chem. Rev., 116, 10075, 10.1021/acs.chemrev.6b00057 Hari, 2014, Synthetic applications of eosin Y in photoredox catalysis, Chem. Commun., 50, 6688, 10.1039/C4CC00751D Zilate, 2020, Design and application of aminoacridinium organophotoredox catalysts, Chem. Commun., 56, 1767, 10.1039/C9CC08524F Shang, 2019, Recent advances of 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) in photocatalytic transformations, Chem. Commun., 55, 5408, 10.1039/C9CC01047E Hlouskova, 2019, Structural elaboration of dicyanopyrazine: towards push–pull molecules with tailored photoredox activity, RSC Adv., 9, 23797, 10.1039/C9RA04731J Jiao, 2021, A donor−acceptor [2]catenane for visible light photocatalysis, J. Am. Chem. Soc., 143, 8000, 10.1021/jacs.1c01493 Wang, 2021, Flowers of the plant genus Hypericum as versatile photoredox catalysts, Green Chem., 23, 881, 10.1039/D0GC03281F Li, 2019, Cercosporin-bioinspired selective photooxidation reactions under mild conditions, Green Chem., 21, 6073, 10.1039/C9GC02270H Wang, 2016, BODIPY catalyzed amide synthesis promoted by BHT and air under visible light, Org. Biomol. Chem., 14, 7028, 10.1039/C6OB00736H Santos, 2021, Dibromo-BODIPY as an organic photocatalyst for radical–ionic sequences, J. Org. Chem., 86, 16315, 10.1021/acs.joc.1c01598 Noto, 2020, Laser flash photolysis studies on radical monofluoromethylation by (diarylamino)naphthalene photoredox catalysis: long lifetime of the excited state is not always a requisite, J. Org. Chem., 85, 13220, 10.1021/acs.joc.0c01999 Vega-Peñaloza, 2020, A rational approach to organo-photocatalysis: novel designs and structure-property relationships, Angew. Chem. Int. Ed., 60, 1082, 10.1002/anie.202006416 Patel, 2021, Visible light-mediated applications of methylene blue in organic synthesis, Org. Chem. Front., 8, 1694, 10.1039/D0QO01182G Brydena, 2021, Colman, organic thermally activated delayed fluorescence (TADF) compounds used in photocatalysis, Chem. Soc. Rev., 50, 7587, 10.1039/D1CS00198A Wei, 2020, Visible-light-mediated aminoquinolate diarylboron-catalyzed metal-free hydroxylation of organoboronic acids under air and room temperature, ACS Sustain. Chem. Eng., 8, 13894, 10.1021/acssuschemeng.0c05121 Zu, 2020, Dual aminoquinolate diarylboron and nickel catalysed metallaphotoredox platform for carbon–oxygen bond construction, Chem. Commun., 56, 8273, 10.1039/D0CC03230A Mei, 2020, Helical carbenium ion: a versatile organic photoredox catalyst for red-light-mediated reactions, J. Am. Chem. Soc., 142, 12056, 10.1021/jacs.0c05507 Luan, 2020, Discovery of oxygen α-nucleophilic addition to α, β-unsaturated amides catalyzed by redox-neutral organic photoreductant, J. Am. Chem. Soc., 142, 20942, 10.1021/jacs.0c10707 Zhang, 2020, Pyrenediones as versatile photocatalysts for oxygenation reactions with in situ generation of hydrogen peroxide under visible light, Green Chem., 22, 22, 10.1039/C9GC03152A Wang, 2021, CBZ6 as a recyclable organic photoreductant for pinacol coupling, Org. Lett., 23, 2900, 10.1021/acs.orglett.1c00537 Kim, 2019, Nicotinamide adenine dinucleotide as a photocatalyst, Sci. Adv., 5, eaax0501, 10.1126/sciadv.aax0501 König, 2018, Flavin photocatalysis, Phys. Sci. Rev., 3, 20170168 Marzo, 2018, Visible-light photocatalysis: does it make a difference in organic synthesis?, Angew. Chem. Int. Ed., 57, 10034, 10.1002/anie.201709766 Zhu, 2020, Recent advances in photoredox and nickel dual-catalyzed cascade reactions: pushing the boundaries of complexity, Chem. Sci., 11, 4051, 10.1039/D0SC00712A Skubi, 2016, Dual catalysis strategies in photochemical synthesis, Chem. Rev., 116, 10035, 10.1021/acs.chemrev.6b00018 Twilton, 2017, The merger of transition metal and photocatalysis, Nat. Rev. Chem., 1, 0052, 10.1038/s41570-017-0052 Reischauer, 2021, Emerging concepts in photocatalytic organic synthesis, iScience, 24, 10.1016/j.isci.2021.102209 Gisbertz, 2020, Overcoming limitations in dual photoredox/nickel-catalysed C–N cross-couplings due to catalyst deactivation, Nat. Catal., 3, 611, 10.1038/s41929-020-0473-6 Kosso, 2021, Cyanine-based near infra-red organic photoredox catalysis, Chem. Sci., 12, 6964, 10.1039/D1SC00998B König, 2017, photocatalysis in organic synthesis – past, present future, Eur. J. Org. Chem., 2017, 1979, 10.1002/ejoc.201700420 Kim, 2020, Site-selective functionalization of methionine residues via photoredox catalysis, J. Am. Chem. Soc., 142, 21260, 10.1021/jacs.0c09926 Adak, 2020, Metal-free, visible-light-enabled direct C3–H arylation of anthranils, Org. Lett., 22, 5640, 10.1021/acs.orglett.0c01999 Teng, 2020, Visible-light-induced regioselective dicarbonylation of indolizines with oxoaldehydes via direct C–H functionalization, Org. Lett., 22, 3841, 10.1021/acs.orglett.0c01094 Walker, 2020, Highly diastereoselective functionalization of piperidines by photoredox-catalyzed α-amino C–H arylation and epimerization, J. Am. Chem. Soc., 142, 8194, 10.1021/jacs.9b13165 Li, 2020, Three-component minisci reaction with 1,3-dicarbonyl compounds induced by visible light, Org. Lett., 22, 2386, 10.1021/acs.orglett.0c00584 Lu, 2019, Visible-light-enabled oxidative coupling of alkenes with dialkylformamides to access unsaturated amides, Org. Lett., 21, 9929, 10.1021/acs.orglett.9b03870 Wang, 2019, Desulfonative photoredox alkylation of N-heteroaryl sulfones – an acid-free approach for substituted heteroarene synthesis, Chem. Sci., 10, 4389, 10.1039/C9SC00776H Guo, 2019, Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions, Chem. Sci., 10, 8792, 10.1039/C9SC03070K Sun, 2020, Metal-free regioselective alkylation of imidazo[1,2-a]pyridines with N-hydroxyphthalimide esters under organic photoredox catalysis, Synlett, 31, 363, 10.1055/s-0039-1691567 Aukland, 2020, Metal-free photoredox-catalysed formal C–H/C–H coupling of arenes enabled by interrupted pummerer activation, Nat. Catal., 3, 163, 10.1038/s41929-019-0415-3 Zhang, 2020, Direct C–H difluoromethylation of heterocycles via organic photoredox catalysis, Nat. Commun., 11, 638, 10.1038/s41467-020-14494-8 Zhu, 2019, Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine, Nat. Commun., 10, 749, 10.1038/s41467-019-08669-1 Lee, 2020, Visible-light-enabled trifluoromethylative pyridylation of alkenes from pyridines and triflic anhydride, Angew. Chem. Int. Ed., 59, 13379, 10.1002/anie.202004439 Abrams, 2020, Photocatalytic difunctionalization of vinyl ureas by radical addition polar truce–smiles rearrangement cascades, Angew. Chem. Int. Ed., 132, 11697, 10.1002/ange.202003632 Murugesan, 2021, Visible-light-promoted metal-free synthesis of (hetero)aromatic nitriles from C(sp3)−H bonds, Angew. Chem. Int. Ed., 60, 2439, 10.1002/anie.202011815 Sap, 2020, Organophotoredox hydrodefluorination of trifluoromethylarenes with translational applicability to drug discovery, J. Am. Chem. Soc, 9181, 10.1021/jacs.0c03881 Graml, 2020, Deazaflavin reductive photocatalysis involves excited semiquinone radicals, Nat. Commun., 11, 3174, 10.1038/s41467-020-16909-y Nakano, 2020, Photoenzymatic hydrogenation of heteroaromatic olefins using ‘ene’-reductases with photoredox catalysts, Angew. Chem. Int. Ed., 59, 10484, 10.1002/anie.202003125 Guo, 2020, Visible-light promoted regioselective amination and alkylation of remote C(sp3)-H bonds, Nat. Commun., 11, 1463, 10.1038/s41467-020-15167-2 Neogi, 2020, Organophotoredox-catalyzed direct C–H amination of 2H-indazoles with amines, Org. Lett., 22, 5605, 10.1021/acs.orglett.0c01973 Singh, 2020, Eosin Y‐catalyzed synthesis of 3–aminoimidazo[1,2–a]pyridines via the HAT process under visible light through formation of the C−N bond, ACS Omega, 5, 29854, 10.1021/acsomega.0c03941 Song, 2020, Visible light-induced amide bond formation, Org. Lett., 22, 371, 10.1021/acs.orglett.9b03905 Guo, 2021, Selective 1,2-aminoisothiocyanation of 1,3-dienes under visible-light photoredox catalysis, Angew. Chem. Int. Ed., 60, 4085, 10.1002/anie.202014518 Jung, 2020, Tuning triplet energy transfer of hydroxamates as the nitrene precursor for intramolecular C(sp3)–H amidation, J. Am. Chem. Soc., 142, 5811, 10.1021/jacs.0c00868 Kang, 2020, Direct C(sp3)–N radical coupling: photocatalytic C–H functionalization by unconventional intermolecular hydrogen atom transfer to aryl radical, Org. Lett., 22, 6112, 10.1021/acs.orglett.0c02179 Zhou, 2020, Metal-free, redox-neutral, site-selective access to heteroarylamine via direct radical–radical cross-coupling powered by visible light photocatalysis, Am. Chem. Soc., 142, 16805, 10.1021/jacs.0c07600 Fu, 2019, Transition metal-free phosphonocarboxylation of alkenes with carbon dioxide via visible-light photoredox catalysis, Nat. Commun., 10, 3592, 10.1038/s41467-019-11528-8 Chen, 2021, Visible-light-induced denitrogenative phosphorylation of benzotriazinones: a metal- and additive-free method for accessing ortho-phosphorylated benzamide derivatives, Green Chem., 23, 296, 10.1039/D0GC03613G Wei, 2020, Visible-light-mediated aminoquinolate diarylboron-catalyzed metal-free hydroxylation of organoboronic acids under air and room temperature, ACS Sustain. Chem. Eng., 8, 13894, 10.1021/acssuschemeng.0c05121 Inoa, 2020, Benzylic hydroperoxidation via visible-light-induced Csp3–H activation, J. Org. Chem., 85, 6181, 10.1021/acs.joc.0c00385 Gan, 2020, Visible-light-promoted oxidative desulphurisation: a strategy for the preparation of unsymmetrical ureas from isothiocyanates and amines using molecular oxygen, Green Chem., 22, 2956, 10.1039/D0GC00070A Rykaczewski, 2020, Visible-light-enabled paternò–büchi reaction via triplet energy transfer for the synthesis of oxetanes, Org. Lett., 22, 6516, 10.1021/acs.orglett.0c02316 Hong, 2020, Oxidative C–S bond cleavage of benzyl thiols enabled by visible-light-mediated silver(II) complexes, Org. Lett., 22, 4395, 10.1021/acs.orglett.0c01399 Choi, 2020, Visible-light-induced cysteine-specific bioconjugation: biocompatible thiol–ene click chemistry, Angew. Chem. Int. Ed., 59, 22514, 10.1002/anie.202010217 Hell, 2020, Hydrosulfonylation of alkenes with sulfonyl chlorides under visible light activation, Angew. Chem. Int. Ed., 59, 11620, 10.1002/anie.202004070 Gadde, 2020, Thiosulfonylation of unactivated alkenes with visible-light organic photocatalysis, ACS Catal., 10, 8765, 10.1021/acscatal.0c02159 Santos, 2020, Photoredox catalysis toward 2-sulfenylindole synthesis through a radical cascade process, Org. Lett, 4266, 10.1021/acs.orglett.0c01297 Kim, 2020, Direct allylic C(sp3)–H thiolation with disulfides via visible light photoredox catalysis, ACS Catal., 10, 6013, 10.1021/acscatal.0c01232 Sandfort, 2020, Site-selective thiolation of (multi)halogenated heteroarenes, J. Am. Chem. Soc., 142, 6913, 10.1021/jacs.0c01630 Huang, 2020, Visible-light-promoted cross-coupling reactions of aryldiazonium salts with S-Methyl-d3 sulfonothioate or Se-methyl-d3 selenium sulfonate: synthesis of trideuteromethylated sulfides, sulfoxides, and selenides, Org. Lett., 22, 9128, 10.1021/acs.orglett.0c03562 Han, 2019, Organic photoredox-catalyzed decarboxylative trifluoromethylselenolation of aliphatic carboxylic acids with [Me4N][SeCF3], Org. Lett., 21, 10013, 10.1021/acs.orglett.9b03941 Herron, 2020, δ-C–H mono- and dihalogenation of alcohols, J. Am. Chem. Soc., 142, 2766, 10.1021/jacs.9b13171 Fu, 2020, Triphenylphosphine-catalyzed alkylative iododecarboxylation with lithium iodide under visible light, Org. Lett., 22, 8572, 10.1021/acs.orglett.0c03173 Chan, 2021, Metallaphotoredox: the merger of photoredox and transition metal catalysis, Chem. Rev. Faraggi, 2021, Synthesis of enantiopure unnatural amino acids by metallaphotoredox catalysis, Org. Process Res. Dev., 25, 1966, 10.1021/acs.oprd.1c00208 Dighe, 2020, A photochemical dehydrogenative strategy for aniline synthesis, Nature, 584, 75, 10.1038/s41586-020-2539-7 Jin, 2015, Alcohols as alkylating agents in heteroarene C–H functionalization, Nature, 525, 87, 10.1038/nature14885 Kuang, 2019, Asymmetric synthesis of 1,4-dicarbonyl compounds from aldehydes by hydrogen atom transfer photocatalysis and chiral lewis acid catalysis, Angew. Chem. Int. Ed., 58, 16859, 10.1002/anie.201910414 Dong, 2021, Enantioselective synthesis of γ‐oxycarbonyl motifs by conjugate addition of photogenerated α‐alkoxy radicals, Org. Lett., 23, 5703, 10.1021/acs.orglett.1c01790