ACS Publications. Most Trusted. Most Cited. Most Read
Synthesis of Sterically Hindered Primary Amines by Concurrent Tandem Photoredox Catalysis
My Activity

Figure 1Loading Img
    Article

    Synthesis of Sterically Hindered Primary Amines by Concurrent Tandem Photoredox Catalysis
    Click to copy article linkArticle link copied!

    Other Access OptionsSupporting Information (1)

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2020, 142, 2, 987–998
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.9b10871
    Published January 6, 2020
    Copyright © 2020 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Primary amines are an important structural motif in active pharmaceutical ingredients (APIs) and intermediates thereof, as well as members of ligand libraries for either biological or catalytic applications. Many chemical methodologies exist for amine synthesis, but the direct synthesis of primary amines with a fully substituted α carbon center is an underdeveloped area. We report a method which utilizes photoredox catalysis to couple readily available O-benzoyl oximes with cyanoarenes to synthesize primary amines with fully substituted α-carbons. We also demonstrate that this method enables the synthesis of amines with α-trifluoromethyl functionality. Based on experimental and computational results, we propose a mechanism where the photocatalyst engages in concurrent tandem catalysis by reacting with the oxime as a triplet sensitizer in the first catalytic cycle and a reductant toward the cyanoarene in the second catalytic cycle to achieve the synthesis of hindered primary amines via heterocoupling of radicals from readily available oximes.

    Copyright © 2020 American Chemical Society

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.9b10871.

    • Synthetic procedures, spectral data, compound characterization, and Cartesian coordinates of computational structures (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai

    This article is cited by 109 publications.

    1. Cheng Huang, Zhong-Ming Ye, Yu-Shu Qin, Gui-Ping You, Zhenhong Wei, Hu Cai. Radical α-C–H Alkylation and Heteroarylation of Benzyl Anilines Enabled by Organic Photoredox Catalysis. Organic Letters 2025, 27 (1) , 275-281. https://doi.org/10.1021/acs.orglett.4c04278
    2. Changduo Pan, Dongdong Chen. Photocatalytic Consecutive Photoinduced Electron Transfer-Enabled C(sp3)–H Pyridylation of Dihydroquinoxalin-2-ones. The Journal of Organic Chemistry 2024, 89 (23) , 17587-17597. https://doi.org/10.1021/acs.joc.4c02328
    3. María Martín, Rafael Martín Romero, Chiara Portolani, Mariola Tortosa. Csp3–Csp2 Coupling of Isonitriles and (Hetero)arenes through a Photoredox-Catalyzed Double Decyanation Process. ACS Catalysis 2024, 14 (23) , 17286-17292. https://doi.org/10.1021/acscatal.4c06269
    4. Bernard G. Stevenson, Cameron Gironda, Eric Talbott, Amanda Prascsak, Nora L. Burnett, Victoria Kompanijec, Roman Nakhamiyayev, Lisa A. Fredin, John R. Swierk. Photoredox Product Selectivity Controlled by Persistent Radical Stability. The Journal of Organic Chemistry 2024, 89 (19) , 13818-13825. https://doi.org/10.1021/acs.joc.3c00490
    5. Conghui Wang, Meizhong Tang, Yating Wang, Shenlin Huang, Lan-Gui Xie. Photoinduced, Redox-Neutral Decyanative and Defluorinative Phosphination of (Hetero)Arenes. Organic Letters 2024, 26 (38) , 8154-8158. https://doi.org/10.1021/acs.orglett.4c03049
    6. Harry C. Waller, Matthew J. Gaunt. Silyl Radicals as Single-Electron Reductants: α-Aminoalkyl Radical Formation via a Photocatalytic Oxidatively Initiated Radical Chain Process. Journal of the American Chemical Society 2024, 146 (38) , 25894-25901. https://doi.org/10.1021/jacs.4c08230
    7. Xiongwen Li, Tiexin Zhang, Jianing Li, Renhai Liu, Yusheng Shi, Cheng He, Chunying Duan. Dye Stacking Goes Beyond Single-Molecule Photocatalysis: Modifying Twisted Segregated Stacking of Dyes in Coordination Polymers for Multiphoton-Driven Potent Reduction and Oxidation. ACS Catalysis 2024, 14 (18) , 13567-13578. https://doi.org/10.1021/acscatal.4c03442
    8. Chenxing Zhou, Dongsheng Ji, Xuxia Wang, Caixia Yang, Pengxin Zhou, Congde Huo. Decyanative Heteroarylations of Glycine Derivatives. Organic Letters 2024, 26 (25) , 5323-5328. https://doi.org/10.1021/acs.orglett.4c01701
    9. Nicholas J. Venditto, Jeffrey A. Boerth. Deoxy-Arylation of Amides via a Tandem Hydrosilylation/Radical– Radical Coupling Sequence. Organic Letters 2024, 26 (17) , 3617-3621. https://doi.org/10.1021/acs.orglett.4c01121
    10. Shouliang Yang, Fen Wang, Stephanie Scales, Michelle Tran-Dubé, Madeline Berry, Haiwei Xu, Feng Tang, Liangliang Xue, Zhongwei Ma, Bryan Li, Indrawan McAlpine. A Disconnection for Rapid Access to Heterocyclic Benzylic Amines with Fully Substituted α-Carbons. The Journal of Organic Chemistry 2024, 89 (6) , 3926-3930. https://doi.org/10.1021/acs.joc.3c02748
    11. Jiaxuan Shen, Jincan Li, Meijun Chen, Xuerong Yue, Xin Shi. Photoinduced Radical Desulfurative C(sp3)–C(sp2) Coupling via Electron Donor–Acceptor Complexes. Organic Letters 2024, 26 (7) , 1495-1500. https://doi.org/10.1021/acs.orglett.4c00162
    12. Cheng Huang, Peng Xiao, Zhong-Ming Ye, Chen-Lu Wang, Chen Kang, Sheng Tang, Zhenhong Wei, Hu Cai. Direct C(sp3)–H Arylation of Unprotected Benzyl Anilines and Alkylarenes by Organocatalysis under Visible Light. Organic Letters 2024, 26 (1) , 304-309. https://doi.org/10.1021/acs.orglett.3c03980
    13. Weijie Deng, Xinling Li, Zhenjie Li, Yating Wen, Ziliang Wang, Zeyin Lin, Yibiao Li, Jinhui Hu, Yubing Huang. Electrochemically Driven C4-Selective Decyanoalkylation of Cyanopyridines with Unactivated Alkyl Bromides Enabling C(sp3)–C(sp2) Coupling. Organic Letters 2023, 25 (51) , 9237-9242. https://doi.org/10.1021/acs.orglett.3c03984
    14. Subrata K. Ghosh, Lizhe He, Zilu Tang, Robert J. Comito. Selective and Functional-Group-Tolerant Photoalkylation of Imines by Energy-Transfer Photocatalysis. The Journal of Organic Chemistry 2023, 88 (21) , 15209-15217. https://doi.org/10.1021/acs.joc.3c01722
    15. Xiaokun Zhang, Chaochun Wei, Dongchen Chu, Hong Yan, Xiuqing Song. Visible-Light-Driven [2 + 2] Photocycloaddition for Constructing Dimers of N,N′-Diacyl-1,4-dihydropyrazines: Experimental and Theoretical Investigation. The Journal of Organic Chemistry 2023, 88 (19) , 13946-13955. https://doi.org/10.1021/acs.joc.3c01516
    16. Xian-Chao Cui, Hu Zhang, Hao Zhang, Yi-Ping Wang, Jian-Ping Qu, Yan-Biao Kang. Synthesis of α-Hydroxyl and α-Amino Pyridinyl Esters via Photoreductive Dual Radical Cross-Coupling. Organic Letters 2023, 25 (39) , 7198-7203. https://doi.org/10.1021/acs.orglett.3c02780
    17. Hongping Zhao, Yuanyuan Hu, Songlin Zheng, Weiming Yuan. α-Tertiary Primary Amine Synthesis via Photocatalytic C(sp3)–H Aminoalkylation. Organic Letters 2023, 25 (36) , 6699-6704. https://doi.org/10.1021/acs.orglett.3c02507
    18. Connor J. Taylor, Alexander Pomberger, Kobi C. Felton, Rachel Grainger, Magda Barecka, Thomas W. Chamberlain, Richard A. Bourne, Christopher N. Johnson, Alexei A. Lapkin. A Brief Introduction to Chemical Reaction Optimization. Chemical Reviews 2023, 123 (6) , 3089-3126. https://doi.org/10.1021/acs.chemrev.2c00798
    19. Weichen Huang, Yongxiang Zheng, Sebastian Keess, Gary A. Molander. A General and Modular Approach to BCP Alkylamines via Multicomponent Difunctionalization of [1.1.1]Propellane. Journal of the American Chemical Society 2023, 145 (9) , 5363-5369. https://doi.org/10.1021/jacs.2c13298
    20. Sina Rezazadeh, Maxwell I. Martin, Raphael S. Kim, Glenn P. A. Yap, Joel Rosenthal, Donald A. Watson. Photoredox-Nickel Dual-Catalyzed C-Alkylation of Secondary Nitroalkanes: Access to Sterically Hindered α-Tertiary Amines. Journal of the American Chemical Society 2023, 145 (8) , 4707-4715. https://doi.org/10.1021/jacs.2c13174
    21. Yanjie Wang, Xia Meng, Changqun Cai, Lingyun Wang, Hang Gong. Radical Cross-Coupling Reaction Based on Hydrogen Atom Abstraction of DMF and Decarboxylation of α-Ketoacid under Electricity. The Journal of Organic Chemistry 2022, 87 (22) , 15042-15049. https://doi.org/10.1021/acs.joc.2c01461
    22. Wei-Mei Zeng, Yan-Hong He, Zhi Guan. Direct Reductive Arylation of Imines with Electron-Deficient (Hetero) Arenes via Electrosynthesis to Access Benzylic Amines. Organic Letters 2022, 24 (39) , 7178-7182. https://doi.org/10.1021/acs.orglett.2c02900
    23. Jiahao Zhu, Donghui Wei, Lili Wang, Zheng Duan. One Stone Three Birds: Regiodivergent Access to Amino-Substituted Benzophospholes and Their Structure–Property Relationships. The Journal of Organic Chemistry 2022, 87 (17) , 11478-11490. https://doi.org/10.1021/acs.joc.2c01078
    24. Michael J. Tilby, Damien F. Dewez, Loïc R. E. Pantaine, Adrian Hall, Carolina Martínez-Lamenca, Michael C. Willis. Photocatalytic Late-Stage Functionalization of Sulfonamides via Sulfonyl Radical Intermediates. ACS Catalysis 2022, 12 (10) , 6060-6067. https://doi.org/10.1021/acscatal.2c01442
    25. Yajuan Li, Cuijie Han, Yanyan Wang, Xin Huang, Xiaowei Zhao, Baokun Qiao, Zhiyong Jiang. Catalytic Asymmetric Reductive Azaarylation of Olefins via Enantioselective Radical Coupling. Journal of the American Chemical Society 2022, 144 (17) , 7805-7814. https://doi.org/10.1021/jacs.2c01458
    26. Hua-Jian Zhou, Jing-Mei Huang. Hydropyridylation of α,β-Unsaturated Esters through Electroreduction of 4-Cyanopyridine. The Journal of Organic Chemistry 2022, 87 (8) , 5328-5338. https://doi.org/10.1021/acs.joc.2c00177
    27. Laura Buglioni, Fabian Raymenants, Aidan Slattery, Stefan D. A. Zondag, Timothy Noël. Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry. Chemical Reviews 2022, 122 (2) , 2752-2906. https://doi.org/10.1021/acs.chemrev.1c00332
    28. Philip R. D. Murray, James H. Cox, Nicholas D. Chiappini, Casey B. Roos, Elizabeth A. McLoughlin, Benjamin G. Hejna, Suong T. Nguyen, Hunter H. Ripberger, Jacob M. Ganley, Elaine Tsui, Nick Y. Shin, Brian Koronkiewicz, Guanqi Qiu, Robert R. Knowles. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis. Chemical Reviews 2022, 122 (2) , 2017-2291. https://doi.org/10.1021/acs.chemrev.1c00374
    29. Nicholas E. S. Tay, Dan Lehnherr, Tomislav Rovis. Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis. Chemical Reviews 2022, 122 (2) , 2487-2649. https://doi.org/10.1021/acs.chemrev.1c00384
    30. Lisa Candish, Karl D. Collins, Gemma C. Cook, James J. Douglas, Adrián Gómez-Suárez, Anais Jolit, Sebastian Keess. Photocatalysis in the Life Science Industry. Chemical Reviews 2022, 122 (2) , 2907-2980. https://doi.org/10.1021/acs.chemrev.1c00416
    31. Kitae Kwon, R. Thomas Simons, Meganathan Nandakumar, Jennifer L. Roizen. Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis. Chemical Reviews 2022, 122 (2) , 2353-2428. https://doi.org/10.1021/acs.chemrev.1c00444
    32. Hannah E. Askey, James D. Grayson, Joshua D. Tibbetts, Jacob C. Turner-Dore, Jake M. Holmes, Gabriele Kociok-Kohn, Gail L. Wrigley, Alexander J. Cresswell. Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines. Journal of the American Chemical Society 2021, 143 (39) , 15936-15945. https://doi.org/10.1021/jacs.1c07401
    33. J. Henry Blackwell, Georgia R. Harris, Milo A. Smith, Matthew J. Gaunt. Modular Photocatalytic Synthesis of α-Trialkyl-α-Tertiary Amines. Journal of the American Chemical Society 2021, 143 (39) , 15946-15959. https://doi.org/10.1021/jacs.1c07402
    34. Xiao Zhang, Chao Yang, Han Gao, Lei Wang, Lin Guo, Wujiong Xia. Reductive Arylation of Aliphatic and Aromatic Aldehydes with Cyanoarenes by Electrolysis for the Synthesis of Alcohols. Organic Letters 2021, 23 (9) , 3472-3476. https://doi.org/10.1021/acs.orglett.1c00920
    35. Dhananjay Yadav, Abhijeet Srivastava, Monish Arbaz Ansari, Maya Shankar Singh. Unusual Behavior of Ketoximes: Reagentless Photochemical Pathway to Alkynyl Sulfides. The Journal of Organic Chemistry 2021, 86 (8) , 5908-5921. https://doi.org/10.1021/acs.joc.1c00417
    36. Ya Bai, Lingling Shi, Lianyou Zheng, Shulin Ning, Xin Che, Zhuoqi Zhang, Jinbao Xiang. Electroselective and Controlled Reduction of Cyclic Imides to Hydroxylactams and Lactams. Organic Letters 2021, 23 (6) , 2298-2302. https://doi.org/10.1021/acs.orglett.1c00430
    37. Lingying Leng, Joseph M. Ready. Photocatalytic α-Alkylation of Amines with Alkyl Halides. ACS Catalysis 2020, 10 (22) , 13196-13201. https://doi.org/10.1021/acscatal.0c04519
    38. Chao Zhou, Tao Lei, Xiang-Zhu Wei, Chen Ye, Zan Liu, Bin Chen, Chen-Ho Tung, Li-Zhu Wu. Metal-Free, Redox-Neutral, Site-Selective Access to Heteroarylamine via Direct Radical–Radical Cross-Coupling Powered by Visible Light Photocatalysis. Journal of the American Chemical Society 2020, 142 (39) , 16805-16813. https://doi.org/10.1021/jacs.0c07600
    39. Alessa B. Rolka, Burkhard Koenig. Dearomative Cycloadditions Utilizing an Organic Photosensitizer: An Alternative to Iridium Catalysis. Organic Letters 2020, 22 (13) , 5035-5040. https://doi.org/10.1021/acs.orglett.0c01622
    40. Kazuhiro Morisaki, Hiroyuki Morimoto, Takashi Ohshima. Recent Progress on Catalytic Addition Reactions to N-Unsubstituted Imines. ACS Catalysis 2020, 10 (12) , 6924-6951. https://doi.org/10.1021/acscatal.0c01212
    41. Jamie A. Leitch, Thomas Rossolini, Tatiana Rogova, J. Andrew P. Maitland, Darren J. Dixon. α-Amino Radicals via Photocatalytic Single-Electron Reduction of Imine Derivatives. ACS Catalysis 2020, 10 (3) , 2009-2025. https://doi.org/10.1021/acscatal.9b05011
    42. Dan Lehnherr, Yu-hong Lam, Michael C. Nicastri, Jinchu Liu, Justin A. Newman, Erik L. Regalado, Daniel A. DiRocco, Tomislav Rovis. Electrochemical Synthesis of Hindered Primary and Secondary Amines via Proton-Coupled Electron Transfer. Journal of the American Chemical Society 2020, 142 (1) , 468-478. https://doi.org/10.1021/jacs.9b10870
    43. Guohui Zeng, Dongwen Guo, Huanfeng Jiang, Biaolin Yin. Chemodivergent dearomatization of benzene-linked O-oxime esters via EnT-induced radical cross-coupling. Chemical Science 2025, 16 (6) , 2690-2699. https://doi.org/10.1039/D4SC07681H
    44. Emily K. Burke, Katherine N. Robertson, Alexander W. H. Speed. Convenient lanthanum-mediated synthesis of bulky tert -alkyl amines from nitriles. Chemical Communications 2025, 144 https://doi.org/10.1039/D4CC05831C
    45. Johannes E. Erchinger, Madina Lenz, Poulami Mukherjee, Yan-Bo Li, Adhya Suresh, Constantin G. Daniliuc, Osvaldo Gutierrez, Frank Glorius. Mechanistic insights into the regiodivergent insertion of bicyclo[1.1.0]butanes towards carbocycle-tethered N-heteroarenes. Chemical Science 2025, 47 https://doi.org/10.1039/D4SC08637F
    46. Jiaheng Fang, Runyan Tian, Jijun Chen, Xinyuan Liu. Research Progress in the Synthesis of α -Tertiary Amines via Radical Strategies. Chinese Journal of Organic Chemistry 2025, 45 (1) , 22. https://doi.org/10.6023/cjoc202406040
    47. Jia-Min Lu, Hui-Feng Wang, Qi-Hang Guo, Jian-Wei Wang, Tong-Tong Li, Ke-Xin Chen, Meng-Ting Zhang, Jian-Bo Chen, Qian-Nuan Shi, Yi Huang, Shao-Wen Shi, Guang-Yong Chen, Jian-Zhang Pan, Zhan Lu, Qun Fang. Roboticized AI-assisted microfluidic photocatalytic synthesis and screening up to 10,000 reactions per day. Nature Communications 2024, 15 (1) https://doi.org/10.1038/s41467-024-53204-6
    48. Gaolei Sun, Wenhui Wei, Xiaowei Zhao, Baokun Qiao, Zhiyong Jiang. Photocatalytic Reductive Azaarenylation of Cyclopropanes via Consecutive Photo‐induced Electron Transfer: A Facile Route to α‐Quaternary Azaarenes †. Chinese Journal of Chemistry 2024, 42 (23) , 3035-3040. https://doi.org/10.1002/cjoc.202400508
    49. Hang Gong, Hongmei Fu, Chao Lu, Changqun Cai. Electro-promoted radical-radical cross-coupling reaction to synthesize sulfonamides. Tetrahedron 2024, 168 , 134315. https://doi.org/10.1016/j.tet.2024.134315
    50. Xianzhou Zheng, Weiming Yuan. Recent Progress in the Photocatalytic Synthesis of α ‐Tertiary Primary Amines. European Journal of Organic Chemistry 2024, 27 (40) https://doi.org/10.1002/ejoc.202400350
    51. Alex A. Rafaniello, Roopender Kumar, Rachel C. Phillips, Matthew J. Gaunt. Modular Synthesis of Heterobenzylic Amines via Carbonyl Azinylative Amination. Angewandte Chemie 2024, 136 (42) https://doi.org/10.1002/ange.202408287
    52. Changduo Pan, Chengli Xiang, Jin-Tao Yu. Organophotocatalytic pyridination of N -arylglycines with 4-cyanopyridines by decarboxylative and decyanative radical–radical coupling. Organic & Biomolecular Chemistry 2024, 22 (38) , 7806-7810. https://doi.org/10.1039/D4OB01257G
    53. Min Liu, Bifu Liu, Hongyan Chen, Qian Wang, Lixin Liu, Kejun Feng, Zijia Wang, Qiang Li. Synthesis of 2 H -imidazoles via copper-catalyzed homo/cross-coupling of oxime acetates. Organic & Biomolecular Chemistry 2024, 22 (36) , 7316-7320. https://doi.org/10.1039/D4OB00977K
    54. Hyunji Min, Yonghwan Kwon, Sukhyun Shin, Miseon Choi, Manish Kumar Mehra, Woojin Jeon, Min Sang Kwon, Chung Whan Lee. Tailoring the Degradation of Cyanoarene‐Based Photocatalysts for Enhanced Visible‐Light‐Driven Halogen Atom Transfer. Angewandte Chemie International Edition 2024, 63 (36) https://doi.org/10.1002/anie.202406880
    55. Hyunji Min, Yonghwan Kwon, Sukhyun Shin, Miseon Choi, Manish Kumar Mehra, Woojin Jeon, Min Sang Kwon, Chung Whan Lee. Tailoring the Degradation of Cyanoarene‐Based Photocatalysts for Enhanced Visible‐Light‐Driven Halogen Atom Transfer. Angewandte Chemie 2024, 136 (36) https://doi.org/10.1002/ange.202406880
    56. Shreya Yadav, Praveen P. Singh, Yogesh Murti, Priyank Purohit, Pravin K. Singh, Vishal Srivastava. Recent advances of 3DPAFIPN in photoredox catalysis. Tetrahedron 2024, 163 , 134138. https://doi.org/10.1016/j.tet.2024.134138
    57. Jiaxuan Shen, Meijun Chen, Jincan Li, Yimin Chen. Visible‐Light‐Induced Three‐Component Alkylpyridylation of Alkenes Enabled by Electron Donor‐Acceptor Complex. Advanced Synthesis & Catalysis 2024, 366 (14) , 3138-3143. https://doi.org/10.1002/adsc.202400322
    58. Alex A. Rafaniello, Roopender Kumar, Rachel C Phillips, Matthew James Gaunt. Modular Synthesis of Heterobenzylic Amines via Carbonyl Azinylative Amination. Angewandte Chemie International Edition 2024, https://doi.org/10.1002/anie.202408287
    59. Nan Cai, Xiang Gao, Wenjing Li, Li Yang, Jinfeng Zhao, Jingping Qu, Yuhan Zhou. Novel trifluoromethyl ketone derivatives as oral cPLA2/COX-2 dual inhibitors for resolution of inflammation in rheumatoid arthritis. Bioorganic Chemistry 2024, 148 , 107453. https://doi.org/10.1016/j.bioorg.2024.107453
    60. Iram Kalsoom, Muhammad Bilal, Aqsa Kanwal, Nasir Rasool, Usman Nazeer, Codrut Ciurea, Andrea Elena Neculau, Carmen Constantina Martinescu. Selective C–C bond cleavage of cycloketoximes via iminyl radicals and distal carbon radicals through photocatalysis. Journal of Saudi Chemical Society 2024, 28 (3) , 101848. https://doi.org/10.1016/j.jscs.2024.101848
    61. Changduo Pan, Dongdong Chen, Yangjian Cheng, Jin-Tao Yu. Photocatalytic redox-neutral α-C(sp 3 )–H pyridination of glycine derivatives and N -arylamines with cyanopyridines. Chemical Communications 2024, 60 (33) , 4451-4454. https://doi.org/10.1039/D4CC00906A
    62. Meng-Jie Zheng, Xu-Kuan Qi, Chao Yang, Lin Guo, Yating Zhao, Wujiong Xia. Photoinduced amination of iodoalkanes enabled by bifunctional O -benzoyl oxime. Organic Chemistry Frontiers 2024, 11 (7) , 1949-1954. https://doi.org/10.1039/D3QO02137H
    63. Manman Kong, Zhuoxi Wang, Xu Ban, Xiaowei Zhao, Yanli Yin, Junmin Zhang, Zhiyong Jiang. Radical Cross Coupling and Enantioselective Protonation through Asymmetric Photoredox Catalysis. Advanced Science 2024, 11 (12) https://doi.org/10.1002/advs.202307773
    64. Fei Chao, Hai‐Bin Yang, Yanxiong Fang. Photoredox‐catalyzed Decyanative Radical Cross‐coupling Reactions of Aromatic Nitriles. ChemCatChem 2024, 24 https://doi.org/10.1002/cctc.202301281
    65. Robin Cauwenbergh, Prakash Kumar Sahoo, Rakesh Maiti, Abra Mathew, Rositha Kuniyil, Shoubhik Das. Selective synthesis of functionalized linear aliphatic primary amines via decarboxylative radical-polar crossover. Green Chemistry 2024, 26 (1) , 264-276. https://doi.org/10.1039/D3GC03187J
    66. Parag Mistry, Subhankar Das, Rik Patra, Indranil Chatterjee. Exploring N-centered umpolung reactivity in photoredox-catalyzed amidation with an α-iminoester. Organic Chemistry Frontiers 2024, 46 https://doi.org/10.1039/D4QO01515K
    67. Jingan Li, Youliang He, Feng Jiang, Xiaoming Wang. Deoxygenative arylation of secondary amides by merging iridium catalysis with electrochemical radical cross-coupling. Green Chemistry 2023, 25 (22) , 9080-9085. https://doi.org/10.1039/D3GC03193D
    68. Hawa Keita, Simon J. Meek. Synthesis of Quaternary and Tertiary Carbon‐Substituted Arenes by Lewis Base Promoted Site‐Selective Coupling with Allylic Nucleophiles. Angewandte Chemie 2023, 135 (34) https://doi.org/10.1002/ange.202306277
    69. Hawa Keita, Simon J. Meek. Synthesis of Quaternary and Tertiary Carbon‐Substituted Arenes by Lewis Base Promoted Site‐Selective Coupling with Allylic Nucleophiles. Angewandte Chemie International Edition 2023, 62 (34) https://doi.org/10.1002/anie.202306277
    70. Jiapian Huang, Zhiyuan Chen. Radical Decyanations of Unactivated Carbon‐CN Bonds: Recent Achievements and Mechanistic Studies. Advanced Synthesis & Catalysis 2023, 365 (13) , 2058-2091. https://doi.org/10.1002/adsc.202300281
    71. Rizvi Syed Aal E Ali, Yilin Zhou, Kai Gong, Xuefeng Jiang. Parallel photoreactor development with enhanced photon efficiency and reproducibility based on laws of optics. Green Synthesis and Catalysis 2023, 4 (2) , 169-172. https://doi.org/10.1016/j.gresc.2022.10.007
    72. Benjamin Cohen, Dan Lehnherr, Melda Sezen-Edmonds, Jacob H. Forstater, Michael O. Frederick, Lin Deng, Antonio C. Ferretti, Kaid Harper, Moiz Diwan. Emerging reaction technologies in pharmaceutical development: Challenges and opportunities in electrochemistry, photochemistry, and biocatalysis. Chemical Engineering Research and Design 2023, 192 , 622-637. https://doi.org/10.1016/j.cherd.2023.02.050
    73. Jiaxuan Shen, Jincan Li, Meijun Chen, Yimin Chen. Photocatalyst-free, metal-free, visible light-induced thiolation/pyridylation of styrenes using an electron donor–acceptor complex as a bifunctional reagent. Organic Chemistry Frontiers 2023, 10 (5) , 1166-1172. https://doi.org/10.1039/D2QO01889F
    74. Cunjing Miao, Jiaqi Yao. Recent Advances in the Transformation Reactions of Aromatic Nitriles via C—CN Bond Cleavage. Chinese Journal of Organic Chemistry 2023, 43 (4) , 1341. https://doi.org/10.6023/cjoc202209007
    75. Lei Yang, Maolin Sun, Liming Cao, Chaoming Liang, Jiasheng Yang, Junjun Yi, Ruihua Cheng, Yueyue Ma, Jinxing Ye. Electricity-driven three-component reductive coupling reaction for the synthesis of diarylmethylamine. Chemical Communications 2022, 58 (96) , 13345-13348. https://doi.org/10.1039/D2CC05330F
    76. Yan Ding, Shengjiao Yu, Man Ren, Ji Lu, Qiang Fu, Zhijie Zhang, Qin Wang, Jun Bai, Na Hao, Lin Yang, Siping Wei, Dong Yi, Jun Wei. Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation. Frontiers in Chemistry 2022, 10 https://doi.org/10.3389/fchem.2022.1059792
    77. Munetaka Akita. Visible‐Light‐Driven CH Bond Functionalization of Amine Derivatives. 2022, 1-35. https://doi.org/10.1002/9783527834242.chf0210
    78. Xian-Chao Cui, Hu Zhang, Yi-Ping Wang, Jian-Ping Qu, Yan-Biao Kang. Synthesis of carbinoxamine via α-C(sp 3 )–H 2-pyridylation of O, S or N-containing compounds enabled by non-D–A-type super organoreductants and sulfoxide- or sulfide HAT reagents. Chemical Science 2022, 13 (37) , 11246-11251. https://doi.org/10.1039/D2SC03504A
    79. Christina Strauch, Sebastian Schroeder, Gwendal Grelier, Meike Niggemann. Homolytic N−S Bond Cleavage in Vinyl Triflimides Enabled by Triplet–Triplet Energy Transfer. Chemistry – A European Journal 2022, 28 (53) https://doi.org/10.1002/chem.202201830
    80. Yan Huang, Qian Zhang, Li-Li Hua, Le-Wu Zhan, Jing Hou, Bin-Dong Li. A versatile catalyst-free redox system mediated by carbon dioxide radical and dimsyl anions. Cell Reports Physical Science 2022, 3 (8) , 100994. https://doi.org/10.1016/j.xcrp.2022.100994
    81. Eleni Georgiou, Davide Spinnato, Kang Chen, Paolo Melchiorre, Kilian Muñiz. Switchable photocatalysis for the chemodivergent benzylation of 4-cyanopyridines. Chemical Science 2022, 13 (27) , 8060-8064. https://doi.org/10.1039/D2SC02698H
    82. Jacob R. Immel, Steven Bloom. carba ‐Nucleopeptides ( c NPs): A Biopharmaceutical Modality Formed through Aqueous Rhodamine B Photoredox Catalysis. Angewandte Chemie 2022, 134 (28) https://doi.org/10.1002/ange.202205606
    83. Jacob R. Immel, Steven Bloom. carba ‐Nucleopeptides ( c NPs): A Biopharmaceutical Modality Formed through Aqueous Rhodamine B Photoredox Catalysis. Angewandte Chemie International Edition 2022, 61 (28) https://doi.org/10.1002/anie.202205606
    84. Sai Rohini Narayanan Kolusu, Manuel Nappi. Metal-free deoxygenative coupling of alcohol-derived benzoates and pyridines for small molecules and DNA-encoded libraries synthesis. Chemical Science 2022, 13 (23) , 6982-6989. https://doi.org/10.1039/D2SC01621D
    85. Weijie Ding, Jie Sheng, Jin Li, Xu Cheng. Electroreductive 4-pyridylation of unsaturated compounds using gaseous ammonia as a hydrogen source. Organic Chemistry Frontiers 2022, 9 (10) , 2634-2639. https://doi.org/10.1039/D2QO00132B
    86. Haoyu Li, Shunsuke Chiba. Synthesis of α-tertiary amines by polysulfide anions photocatalysis via single-electron transfer and hydrogen atom transfer in relays. Chem Catalysis 2022, 2 (5) , 1128-1142. https://doi.org/10.1016/j.checat.2022.03.006
    87. Chao Zhou, Qi‐Chao Gan, Tai‐Ping Zhou, Tao Lei, Chen Ye, Xiao‐Jun He, Bin Chen, Heng Lu, Qian Wan, Rong‐Zhen Liao, Chen‐Ho Tung, Li‐Zhu Wu. Site‐Selective N ‐1 and C‐3 Heteroarylation of Indole with Heteroarylnitriles by Organocatalysis under Visible Light. Angewandte Chemie 2022, 134 (10) https://doi.org/10.1002/ange.202116421
    88. Chao Zhou, Qi‐Chao Gan, Tai‐Ping Zhou, Tao Lei, Chen Ye, Xiao‐Jun He, Bin Chen, Heng Lu, Qian Wan, Rong‐Zhen Liao, Chen‐Ho Tung, Li‐Zhu Wu. Site‐Selective N ‐1 and C‐3 Heteroarylation of Indole with Heteroarylnitriles by Organocatalysis under Visible Light. Angewandte Chemie International Edition 2022, 61 (10) https://doi.org/10.1002/anie.202116421
    89. Jiahua Chen, Jun Wei Lim, Derek Yiren Ong, Shunsuke Chiba. Iterative addition of carbon nucleophiles to N , N -dialkyl carboxamides for synthesis of α-tertiary amines. Chemical Science 2021, 13 (1) , 99-104. https://doi.org/10.1039/D1SC05876B
    90. Byeongseok Kweon, Changha Kim, Seonyul Kim, Sungwoo Hong. Remote C−H Pyridylation of Hydroxamates through Direct Photoexcitation of O ‐Aryl Oxime Pyridinium Intermediates. Angewandte Chemie 2021, 133 (51) , 27017-27025. https://doi.org/10.1002/ange.202112364
    91. Byeongseok Kweon, Changha Kim, Seonyul Kim, Sungwoo Hong. Remote C−H Pyridylation of Hydroxamates through Direct Photoexcitation of O ‐Aryl Oxime Pyridinium Intermediates. Angewandte Chemie International Edition 2021, 60 (51) , 26813-26821. https://doi.org/10.1002/anie.202112364
    92. Jan P. Menzel, Benjamin B. Noble, James P. Blinco, Christopher Barner-Kowollik. Predicting wavelength-dependent photochemical reactivity and selectivity. Nature Communications 2021, 12 (1) https://doi.org/10.1038/s41467-021-21797-x
    93. Jacob W. Greenwood, Benjamin T. Boyle, Andrew McNally. Pyridylphosphonium salts as alternatives to cyanopyridines in radical–radical coupling reactions. Chemical Science 2021, 12 (31) , 10538-10543. https://doi.org/10.1039/D1SC02324A
    94. Bo Huang, Zhe Tan. Host-Guest Interactions Between Metal–Organic Frameworks and Air-Sensitive Complexes at High Temperature. Frontiers in Chemistry 2021, 9 https://doi.org/10.3389/fchem.2021.706942
    95. Megan Amy Bryden, Eli Zysman-Colman. Organic thermally activated delayed fluorescence (TADF) compounds used in photocatalysis. Chemical Society Reviews 2021, 50 (13) , 7587-7680. https://doi.org/10.1039/D1CS00198A
    96. Shruti A. Biyani, Yuta W. Moriuchi, David H. Thompson. Advancement in Organic Synthesis Through High Throughput Experimentation. Chemistry–Methods 2021, 1 (7) , 323-339. https://doi.org/10.1002/cmtd.202100023
    97. Tsubasa Nakashima, Haruka Fujimori, Kohsuke Ohmatsu, Takashi Ooi. Exploiting Transient Radical Cations as Brønsted Acids for Allylic C–H Heteroarylation of Enol Silyl Ethers. Chemistry – A European Journal 2021, 27 (36) , 9253-9256. https://doi.org/10.1002/chem.202101352
    98. Shiqi Tong, Kewei Li, Xuanhui Ouyang, Renjie Song, Jinheng Li. Recent advances in the radical-mediated decyanative alkylation of cyano(hetero)arene. Green Synthesis and Catalysis 2021, 2 (2) , 145-155. https://doi.org/10.1016/j.gresc.2021.04.003
    99. Ana Koperniku, Laurel L. Schafer. Zirconium Catalyzed Hydroaminoalkylation for the Synthesis of α‐Arylated Amines and N‐Heterocycles. Chemistry – A European Journal 2021, 27 (20) , 6334-6339. https://doi.org/10.1002/chem.202100014
    100. Jiaxuan Shen, Yipin Zhang, Yanjiang Yu, Manman Wang. Metal-free visible-light-induced photoredox-catalyzed intermolecular pyridylation/phosphinoylation of alkenes. Organic Chemistry Frontiers 2021, 8 (5) , 901-907. https://doi.org/10.1039/D0QO01218A
    Load all citations

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2020, 142, 2, 987–998
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.9b10871
    Published January 6, 2020
    Copyright © 2020 American Chemical Society

    Article Views

    17k

    Altmetric

    -

    Citations

    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.