(1) Oda, M.; Oikawa, H.; Kanao, Y.; Yamamuro, A. Preferential Photochemical Cyclobutane-Ring Formations of 2-Cyclohexene-1,4-Dione with Olefins and Acetylenes. A Simple and General Synthesis of Bicyclo[4.2.0]Octane-2,5- Diones. Tetrahedron Lett. 1978, 19 (49), 4905–4908.
(2) Wöhler, F. Ueber Künstliche Bildung Des Harnstoffs. Ann. Chim. Phys. 1828, 88 (2), 253–256.
(3) Lu, Z.; Yoon, T. P. Visible Light Photocatalysis of [2+2] Styrene Cycloadditions by Energy Transfer. Angew. Chemie - Int. Ed. 2012, 51 (41), 10329–10332.
(4) Blanksby, S. J.; Ellison, G. B. Bond Dissociation Energies of Organic Molecules. Acc. Chem. Res. 2003, 36 (4), 255–263.
(5) Kamijo, S.; Kamijo, K.; Maruoka, K.; Murafuji, T. Aryl Ketone Catalyzed Radical Allylation of C(Sp3)-H Bonds under Photoirradiation. Org. Lett. 2016, 18 (24), 6516–6519.
(6) Romero, N. A.; Nicewicz, D. A. Organic Photoredox Catalysis. Chem. Rev. 2016, 116 (17), 10075–10166.
(7) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis. Chem. Rev. 2013, 113 (7), 5322–5363.
(8) Xuan, J.; Xiao, W. J. Visible-Light Photoredox Catalysis. Angew. Chemie - Int. Ed. 2012, 51 (28), 6828–6838.
(9) Ohkubo, K.; Mizushima, K.; Fukuzumi, S. Oxygenation and Chlorination of Aromatic Hydrocarbons with Hydrochloric Acid Photosensitized by 9-Mesityl-10-Methylacridinium under Visible Light Irradiation. Res. Chem. Intermed. 2013, 39 (1), 205–220.
(10) Nguyen, J. D.; D’Amato, E. M.; Narayanam, J. M. R.; Stephenson, C. R. J. Engaging Unactivated Alkyl, Alkenyl and Aryl Iodides in Visible-Light- Mediated Free Radical Reactions. Nat. Chem. 2012, 4 (10), 854–859.
(11) Pause, L.; Robert, M.; Savéant, J. M. Can Single-Electron Transfer Break an Aromatic Carbon - Heteroatom Bond in One Step? A Novel Example of Transition between Stepwise and Concerted Mechanisms in the Reduction of Aromatic Iodides [5]. J. Am. Chem. Soc. 1999, 121 (30), 7158–7159.
(12) Isse, A. A.; Mussini, P. R.; Gennaro, A. New Insights into Electrocatalysis and Dissociative Electron Transfer Mechanisms: The Case of Aromatic Bromides. J. Phys. Chem. C 2009, 113 (33), 14983–14992.
(13) Yin, H.; Jin, Y.; Hertzog, J. E.; Mullane, K. C.; Carroll, P. J.; Manor, B. C.; Anna, J. M.; Schelter, E. J. The Hexachlorocerate(III) Anion: A Potent, Benchtop Stable, and Readily Available Ultraviolet A Photosensitizer for Aryl Chlorides. J. Am. Chem. Soc. 2016, 138 (50), 16266–16273.
(14) Cheng, Y.; Gu, X.; Li, P. Visible-Light Photoredox in Homolytic Aromatic Substitution: Direct Arylation of Arenes with Aryl Halides. Org. Lett. 2013, 15 (11), 2664–2667.
(15) Noto, N.; Koike, T.; Akita, M. Visible-Light-Triggered Monofluoromethylation of Alkenes by Strongly Reducing 1,4-Bis(Diphenylamino)Naphthalene Photoredox Catalysis. ACS Catal. 2019, 9 (5), 4382–4387.
(16) Theriot, J. C.; Lim, C.-H.; Yang, H.; Ryan, M. D.; Musgrave, C. B.; Miyake, G. M. Organocatalyzed Atom Transfer Radical Polymerization Driven by Visible Light. Science (80-. ). 2016, 352 (6289), 1082–1086.
(17) Okamoto, S.; Kojiyama, K.; Tsujioka, H.; Sudo, A. Metal-Free Reductive Coupling of CO and CN Bonds Driven by Visible Light: Use of Perylene as a Simple Photoredox Catalyst. Chem. Commun. 2016, 52 (76), 11339–11342.
(18) Treat, N. J.; Sprafke, H.; Kramer, J. W.; Clark, P. G.; Barton, B. E.; Read De Alaniz, J.; Fors, B. P.; Hawker, C. J. Metal-Free Atom Transfer Radical Polymerization. J. Am. Chem. Soc. 2014, 136 (45), 16096–16101.
(19) Murayama, T.; Carlson, F. Organic Toreceptors Photoconductive Materials Used for Electrophotographic Organic Electrophotography Is One of the Most Prevalent Copier and Printer Technologies . Photoreceptors Play a Major Role in the Electrophotographic Process . Nowadays , Organic P. 有機合成化学協会誌 1999, 57 (6), 541–551.
(20) Luo, J.; Zhang, J. Donor-Acceptor Fluorophores for Visible-Light-Promoted Organic Synthesis: Photoredox/Ni Dual Catalytic C(Sp3)-C(Sp2) Cross- Coupling. ACS Catal. 2016, 6 (2), 873–877.
(21) Uoyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Highly Efficient Organic Light-Emitting Diodes from Delayed Fluorescence. Nature 2012, 492 (7428), 234–238.
(22) Saito, I.; Ikehira, H.; Kasatani, R.; Watanabe, M.; Matsuura, T. Selective Deoxygenation of Secondary Alcohols by Photosensitized Electron-Transfer Reaction. A General Procedure for Deoxygenation of Ribonucleosides 1. J. Am. Chem. Soc. 1986, 108 (11), 3115–3117.
(23) Prudhomme, D. R.; Wang, Z.; Rizzo, C. J. An Improved Photosensitizer for the Photoinduced Electron-Transfer Deoxygenation of Benzoates and m - (Trifluoromethyl)Benzoates . J. Org. Chem. 1997, 62 (23), 8257–8260.
(24) Shen, B.; Bedore, M. W.; Sniady, A.; Jamison, T. F. Continuous Flow Photocatalysis Enhanced Using an Aluminum Mirror: Rapid and Selective Synthesis of 2′-Deoxy and 2′,3′-Dideoxynucleosides. Chem. Commun. 2012, 48 (60), 7444–7446.
(25) Matsubara, R.; Shin, Y. S.; Shimada, T.; Hayashi, M. Revisiting the Saito Photochemical Reduction and the Development of a One-Pot Deoxygenation of Alcohols. Asian J. Org. Chem. 2014, 3 (10), 1054–1057.
(26) Matsubara, R.; Shimada, T.; Kobori, Y.; Yabuta, T.; Osakai, T.; Hayashi, M. Photoinduced Charge-Transfer State of 4-Carbazolyl-3-(Trifluoromethyl)Benzoic Acid: Photophysical Property and Application to Reduction of Carbon−Halogen Bonds as a Sensitizer. Chem. - An Asian J. 2016, 11 (14), 2006–2010.
(27) Matsubara, R.; Yabuta, T.; Md Idros, U.; Hayashi, M.; Ema, F.; Kobori, Y.; Sakata, K. UVA- and Visible-Light-Mediated Generation of Carbon Radicals from Organochlorides Using Nonmetal Photocatalyst. J. Org. Chem. 2018, 83 (16), 9381–9390.
(28) Zakzeski, J.; Bruijnincx, P. C. A.; Jongerius, A. L.; Weckhuysen, B. M. The Catalytic Valorization of Lignin for the Production of Renewable Chemicals. Chem. Rev. 2010, 110 (6), 3552–3599.
(29) Dermer, O. C. Metallic Salts of Alcohols and Alcohol Analogs. Chem. Rev. 1934, 14 (3), 385–430.
(30) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. Air Stable, Sterically Hindered Ferrocenyl Dialkylphosphines for Palladium-Catalyzed C-C, C-N, and C-O Bond-Forming Cross-Couplings. J. Org. Chem. 2002, 67 (16), 5553–5566.
(31) Narayanam, J. M. R.; Stephenson, C. R. J. Visible Light Photoredox Catalysis: Applications in Organic Synthesis. Chem. Soc. Rev. 2011, 40 (1), 102–113.
(32) Hasegawa, E.; Takizawa, S.; Seida, T.; Yamaguchi, A.; Yamaguchi, N.; Chiba, N.; Takahashi, T.; Ikeda, H.; Akiyama, K. Photoinduced Electron-Transfer Systems Consisting of Electron-Donating Pyrenes or Anthracenes and Benzimidazolines for Reductive Transformation of Carbonyl Compounds. Tetrahedron 2006, 62 (27), 6581–6588.
(33) Larraufie, M. H.; Pellet, R.; Fensterbank, L.; Goddard, J. P.; Lacôte, E.; Malacria, M.; Ollivier, C. Visible-Light-Induced Photoreductive Generation of Radicals from Epoxides and Aziridines. Angew. Chemie - Int. Ed. 2011, 50 (19), 4463–4466.
(34) Todorov, A. R.; Aikonen, S.; Muuronen, M.; Helaja, J. Visible-Light- Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant. Org. Lett. 2019, 21 (10), 3764–3768.
(35) Nguyen, J. D.; Matsuura, B. S.; Stephenson, C. R. J. A Photochemical Strategy for Lignin Degradation at Room Temperature. J. Am. Chem. Soc. 2014, 136 (4), 1218–1221.
(36) Magallanes, G.; Kärkäs, M. D.; Bosque, I.; Lee, S.; Maldonado, S.; Stephenson, C. R. J. Selective C-O Bond Cleavage of Lignin Systems and Polymers Enabled by Sequential Palladium-Catalyzed Aerobic Oxidation and Visible-Light Photoredox Catalysis. ACS Catal. 2019, 9 (3), 2252–2260.
(37) Yang, C.; Kärkäs, M. D.; Magallanes, G.; Chan, K.; Stephenson, C. R. J. Organocatalytic Approach to Photochemical Lignin Fragmentation. Org. Lett. 2020, 22 (20), 8082–8085.
(38) Liang, K.; Liu, Q.; Shen, L.; Li, X.; Wei, D.; Zheng, L.; Xia, C. Intermolecular Oxyarylation of Olefins with Aryl Halides and TEMPOH Catalyzed by the Phenolate Anion under Visible Light. Chem. Sci. 2020, 11 (27), 6996–7002.
(39) Schmalzbauer, M.; Marcon, M.; König, B. Excited State Anions in Organic Transformations. Angew. Chemie Int. Ed. 2020. in printed.
(40) Rehm, D.; Weller, A. Kinetics of Fluorescence Quenching by Electron and H- Atom Transfer. Isr. J. Chem. 1970, 8 (2), 259–271.
(41) Jin, S.; Dang, H. T.; Haug, G. C.; He, R.; Nguyen, V. D.; Nguyen, V. T.; Arman, H. D.; Schanze, K. S.; Larionov, O. V. Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds. J. Am. Chem. Soc. 2020, 142 (3), 1603–1613.
(42) Brimioulle, R.; Bach, T. Enantioselective Lewis Acid Catalysis of Intramolecular Enone [2+2] Photocycloaddition Reactions. Science (80-. ). 2013, 342 (6160), 840–843.
(43) Qin, P. T.; Sun, J.; Wang, F.; Wang, J. Y.; Wang, H.; Zhou, M. D. Visible-Light- Induced C2 Alkylation of Heterocyclic N-Oxides with N-Hydroxyphthalimide Esters under Metal-Free Conditions. Adv. Synth. Catal. 2020, 362 (21), 4707–4715.
(44) Gentry, E. C.; Knowles, R. R. Synthetic Applications of Proton-Coupled Electron Transfer. Acc. Chem. Res. 2016, 49 (8), 1546–1556.
(45) Tsang, W. Thermodynamic and Kinetic Properties of the Cyclohexadienyl Radical. J. Phys. Chem. 1986, 90 (6), 1152–1155.
(46) Bordwell, F. G.; Liu, W. Z. Effects of Sulfenyl, Sulfinyl and Sulfonyl Groups on Acidities and Homolytic Bond Dissociation Energies of Adjacent C-H and N-H Bonds. J. Phys. Org. Chem. 1998, 11 (6), 397–406.
(47) Bordwell, F. G.; Zhang, X.; Cheng, J. P. Comparisons of the Acidities and Homolytic Bond Dissociation Energies of the Acidic N-H and C-H Bonds in Diphenylmethanes and Carbazoles. J. Org. Chem. 1991, 56 (10), 3216–3219.
(48) Budén, M. E.; Bardagí, J. I.; Puiatti, M.; Rossi, R. A. Initiation in Photoredox C- H Functionalization Reactions. Is Dimsyl Anion a Key Ingredient? J. Org. Chem. 2017, 82 (16), 8325–8333.
(49) Gennett, T.; Milner, D. F.; Weaver, M. J. Role of Solvent Reorganization Dynamics in Electron-Transfer Processes. Theory-Experiment Comparisons for Electrochemical and Homogeneous Electron Exchange Involving Metallocene Redox Couples. J. Phys. Chem. 1985, 89 (13), 2787–2794.
(50) Mao, Y.; Liu, Y.; Hu, Y.; Wang, L.; Zhang, S.; Wang, W. Pd-Catalyzed Debenzylation and Deallylation of Ethers and Esters with Sodium Hydride. ACS Catal. 2018, 8 (4), 3016–3020.
(51) Swanger, S. A.; Vance, K. M.; Acker, T. M.; Zimmerman, S. S.; DiRaddo, J. O.; Myers, S. J.; Bundgaard, C.; Mosley, C. A.; Summer, S. L.; Menaldino, D. S.; Jensen, H. S.; Liotta, D. C.; Traynelis, S. F. A Novel Negative Allosteric Modulator Selective for GluN2C/2D-Containing NMDA Receptors Inhibits Synaptic Transmission in Hippocampal Interneurons. ACS Chem. Neurosci. 2018, 9 (2), 306–319.
(52) Shigeno, M.; Hayashi, K.; Nozawa-Kumada, K.; Kondo, Y. Phosphazene Base TBu-P4 Catalyzed Methoxy–Alkoxy Exchange Reaction on (Hetero)Arenes. Chem. - A Eur. J. 2019, 25 (24), 6077–6081.
(53) Percec, V.; Golding, G. M.; Smidrkal, J.; Weichold, O. NiCl2(Dppe)-Catalyzed Cross-Coupling of Aryl Mesylates, Arenesulfonates, and Halides with Arylboronic Acids. J. Org. Chem. 2004, 69 (10), 3447–3452.
(54) Li, G.; Nieves-Quinones, Y.; Zhang, H.; Liang, Q.; Su, S.; Liu, Q.; Kozlowski, M. C.; Jia, T. Transition-Metal-Free Formal Cross-Coupling of Aryl Methyl Sulfoxides and Alcohols via Nucleophilic Activation of C-S Bond. Nat. Commun. 2020, 11 (1), 1–9.
(55) Kuwano, R.; Kusano, H. Benzyl Protection of Phenols under Neutral Conditions: Palladium-Catalyzed Benzylations of Phenols. Org. Lett. 2008, 10 (10), 1979–1982.
(56) Escobar, R. A.; Johannes, J. W. A Unified and Practical Method for Carbon– Heteroatom Cross-Coupling Using Nickel/Photo Dual Catalysis. Chem. - A Eur. J. 2020, 26 (23), 5168–5173.
(57) Urgoitia, G.; SanMartin, R.; Herrero, M. T.; Domínguez, E. Vanadium-Catalyzed Oxidative Debenzylation of O-Benzyl Ethers at Ppm Level. Adv. Synth. Catal. 2016, 358 (20), 3307–3312.
(58) Seo, M.; Kim, J. H.; Seo, G.; Shin, C. H.; Kim, S. Y. Utilization of Evaporation during the Crystallization Process: Self-Templation of Organic Parallelogrammatic Pipes. Chem. - A Eur. J. 2009, 15 (3), 612–622.
(59) Lee, J.; Kang, S. U.; Lim, J. O.; Choi, H. K.; Jin, M. K.; Toth, A.; Pearce, L. V.; Tran, R.; Wang, Y.; Szabo, T.; Blumberg, P. M. N-[4- (Methylsulfonylamino)Benzyl]Thiourea Analogues as Vanilloid Receptor Antagonists: Analysis of Structure-Activity Relationships for the “C-Region.” Bioorganic Med. Chem. 2004, 12 (2), 371–385.
(60) Willett, K. L.; Hites, R. A. Chemical Actinometry: Using o-Nitrobenzaldehyde to Measure Light Intensity in Photochemical Experiments. J. Chem. Educ. 2000, 77 (7), 900–902.
(61) Tao, Y.; Chen, R.; Li, H.; Yuan, J.; Wan, Y.; Jiang, H.; Chen, C.; Si, Y.; Zheng, C.; Yang, B.; Xing, G.; Huang, W. Resonance-Activated Spin-Flipping for Efficient Organic Ultralong Room-Temperature Phosphorescence. Adv. Mater. 2018, 30 (44), 1803856.
(62) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Throssell, K.; Montgomery Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M. J.; Heyd, J. J.; Brothers, E. N.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A. P.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Startmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Gaussian, Inc., Wallingford, CT, 2009.
(63) Tsuneda, T.; Hirao, K. Long-Range Correction for Density Functional Theory. Wiley Interdiscip. Rev. Comput. Mol. Sci. 2014, 4 (4), 375–390.
(64) Tsuneda, T.; Song, J. W.; Suzuki, S.; Hirao, K. On Koopmans’ Theorem in Density Functional Theory. J. Chem. Phys. 2010, 133 (17).
(65) Tsuneda, T.; Singh, R. K. Reactivity Index Based on Orbital Energies. J. Comput. Chem. 2014, 35 (14), 1093–1100.
(66) Tomasi, J.; Mennucci, B.; Cammi, R. Quantum Mechanical Continuum Solvation Models. Chem. Rev. 2005, 105 (8), 2999–3093.
(67) Legault, C. Y. CYLview, 1.0b, Université de Sherbrooke, 2009.
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