Journal of the American Chemical Society
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Complex Pyridines and Diazines. Angew. Chem., Int. Ed. 2017, 56, 9833. (c) Dolewski, R. D.; Fricke, P. J.; McNally, A. Site-Selective
Switching Strategies to Functionalize Polyazines. J. Am. Chem. Soc. 2018, 140, 8020.
(10) For selected recent reviews, see: (a) Narayanam, J. M. R.; Stephenson, C. R. J. Visible Light Photoredox Catalysis: Application in Organic
Synthesis. Chem. Soc. Rev. 2011, 40, 102. (b) 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, 5322. (c) Koike, T.; Akita, M. Visible-Light Radical
Reaction Designed by Ru- and Ir-based Photoredox Catalysis. Inorg. Chem. Front. 2014, 1, 562. (d) Chen, J.-R.; Hu, X- Q.; Lu, L.-Q.; Xiao,
W.-J. Exploration of Visible-Light Photocatalysis in Heterocycle Synthesis and Functionalization: Reaction Design and Beyond. Acc. Chem.
Res. 2016, 49, 1911. (e) Ghosh, I.; Marzo, L.; Das, A.; Shaikh, R.; König, B. Visible Light Mediated Photoredox Catalytic Arylation Reactions.
Acc. Chem. Res. 2016, 49, 1566. (f) Hopkinson, M. N.; Tlahuext-Aca, A.; Glorius, F. Merging Visible Light Photoredox and Gold Catalysis.
Acc. Chem. Res. 2016, 49, 2261. (g) Majek, M.; Jacobi von Wangelin, A. Mechanistic Perspectives on Organic Photoredox Catalysis for
Aromatic Substitutions. Acc. Chem. Res. 2016, 49, 2316. (h) Reiser, O. Shining Light on Copper: Unique Opportunities for Visible-Light-
Catalyzed Atom Transfer Radical Addition Reactions and Related Processes. Acc. Chem. Res. 2016, 49, 1990. (i) Romero, N. A.; Nicewicz,
D. A. Organic Photoredox Catalysis. Chem. Rev. 2016, 116, 10075. (j) Skubi, K. L.; Blum, T. R.; Yoon, T. P. Dual Catalysis Strategies in
Photochemical Synthesis. Chem. Rev. 2016, 116, 10035. (k) Kim, H. J.; Kim, M. Visible Light‐Mediated Installation of Halogen
Functionalities into Multiple Bond Systems. ChemistrySelect 2017, 2, 9136. (l) Cai, B.-G.; Xuan, J.; Xiao, W.-J. Visible Light-Mediated C–P
Bond Formation Reactions. Sci. Bull. 2019, 64, 337. (m) Schultz, D. M.; Yoon, T. P. Solar Synthesis: Prospects in Visible Light Photocatalysis.
Science 2014, 343, 1239176. (n) Xi, Y.; Yi, H.; Lei, A. Synthetic Applications of Photoredox Catalysis with Visible Light. Org. Biomol. Chem.
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013, 11, 2387. (o) Yi, H.; Zhang, G.; Wang, H.; Huang, Z.; Wang, J.; Singh, A. K.; Lei, A. Recent Advances in Radical C–H
Activation/Radical Cross-Coupling. Chem. Rev. 2017, 117, 9016.
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11) For selected examples of photocatalysis, see: (a) Allen, L. J.; Cabrera, P. J.; Lee, M.; Sanford. M. S. N-Acyloxyphthalimides as Nitrogen
Radical Precursors in the Visible Light Photocatalyzed Room Temperature C–H Amination of Arenes and Heteroarenes. J. Am. Chem. Soc.
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014, 136, 5607. (b) Masuda, Y.; Ishida, N.; Murakami, M. Light-Driven Carboxylation of o-Alkylphenyl Ketones with CO . J. Am. Chem.
Soc. 2015, 137, 14063. (c) Choi, G. J.; Zhu, Q.; Miller, D. C.; Gu, C. J.; Knowles, R. R. Catalytic Alkylation of Remote C–H Bonds Enabled
by Proton-Coupled Electron Transfer. Nature 2016, 539, 268. (d) Chu, J. C. K.; Rovis, T. Amide-Directed Photoredox-Catalysed C–C Bond
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Formation at Unactivated sp C–H Bonds. Nature 2016, 539, 272. (e) Zhao, W.; Wurz, R. P.; Peters, J. C.; Fu, G. C. Photoinduced, Copper-
Catalyzed Decarboxylative C–N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement. J. Am. Chem. Soc.
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017, 139, 12153. (f) Zhou, R.; Liu, H.; Tao, H.; Yu, X.; Wu, J. Metal-Free Direct Alkylation of Unfunctionalized Allylic/benzylic sp C–H
Bonds via Photoredox Induced Radical Cation Deprotonation. Chem. Sci. 2017, 8, 4654. (g) Silvi, M.; Verrier, C.; Rey, Y. P.; Buzzetti, L.;
Melchiorre, P. Visible-Light Excitation of Iminium Ions Enables the Enantioselective Catalytic β-Alkylation of Enals. Nat. Chem. 2017, 9,
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868. (h) Vara, B. A.; Jouffroy, M.; Molander, G. A. C(sp )–C(sp ) Cross-Coupling of Alkylsilicates with Borylated Aryl Bromides – An
Iterative Platform to Alkylated Aryl- and Heteroaryl Boronates. Chem. Sci. 2017, 8, 530. (i) Yang, S.; Li, P.; Wang, Z.; Wang, L. Photoinduced
Oxidative Formylation of N,N-Dimethylanilines with Molecular Oxygen without External Photocatalyst. Org. Lett. 2017, 19, 3386. (j) Moon,
Y.; Jang, E.; Choi, S.; Hong, S. Visible-Light-Photocatalyzed Synthesis of Phenanthridinones and Quinolinones via Direct Oxidative C–H
Amidation. Org. Lett. 2018, 20, 240. (k) Shu, W.; Merino, E.; Nevado, C. Visible Light Mediated, Redox Neutral Remote 1,6-
Difunctionalizations of Alkenes. ACS Catal. 2018, 8, 6401. (l) Morcillo, S. P.; Dauncey, E. M.; Kim, J. H.; Douglas, J. J.; Sheisk, N. S.;
Leonori, D. Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen Radicals. Angew. Chem., Int. Ed.
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018, 57, 12945. (m) Hu, X.; Zhang, G.; Bu, F.; Luo, X.; Yi, K.; Zhang, H.; Lei, A. Photoinduced Oxidative Activation of Electron-Rich
Arenes: Alkenylation with H
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Evolution Under External Oxidant-Free Conditions. Chem. Sci. 2018, 9, 1521. (n) Lee, G. S..; Hong, S. H.
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Formal Giese Addition of C(sp )–H Nucleophiles Enabled by Visible Light Mediated Ni Catalysis of Triplet Enone Diradicals. Chem. Sci.
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018, 9, 5810. (o) Barthelemy, A.-L.; Tuccio, B.; Magnier, E.; Dagousset, G. Alkoxyl Radicals Generated under Photoredox Catalysis: A
Strategy for anti‐Markovnikov Alkoxylation Reactions. Angew. Chem., Int. Ed. 2018, 57, 13790. (p) Zhang, L.; Zhang, G.; Li, Y.; Wang, S.;
Lei, A. The Synergistic Effect of Self-Assembly and Visible-Light Induced the Oxidative C–H Acylation of N-Heterocyclic Aromatic
Compounds with Aldehydes. Chem. Commun. 2018, 54, 5744.
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12) Quint, V.; Morlet-Savary, F.; Lohier, J.-F.; Lalevée, J.; Gaumont, A.-C.; Lakhdar, S. Metal-Free, Visible Light-Photocatalyzed Synthesis
of Benzo[b]phosphole Oxides: Synthetic and Mechanistic Investigations. J. Am. Chem. Soc. 2016, 138, 7436.
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13) (a) Kim, K.; Choi, H.; Kang, D.; Hong, S. Visible-Light Excitation of Quinolinone-Containing Substrates Enables Divergent Radical
Cyclizations. Org. Lett. 2019, 21, 3417. (b) Kim, Y.; Lee, K.; Mathi, G. R.; Kim, I.; Hong, S. Visible-Light-Induced Cascade Radical Ring-
Closure and Pyridylation for the Synthesis of Tetrahydrofurans. Green Chem. 2019, 21, 2082. (c) Kim, I.; Park, B.; Kang, G.; Kim, J.; Jung,
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H.; Lee, H.; Baik, M.-H.; Hong, S. Visible-Light-Induced Pyridylation of Remote C(sp )–H Bonds by Radical Translocation of N-
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