Photoredox catalyzed reductive trifluoromethylation of imines via a radical umpolung strategy

被引:0
|
作者
Paul, Hrishikesh [1 ]
Das, Dibyangshu [1 ]
Ariyan, S.K. [1 ]
Pradhan, Suman [1 ]
Chatterjee, Indranil [1 ]
机构
[1] Department of Chemistry, Indian Institute of Technology Ropar, Nangal Road, Punjab, Rupnagar,140001, India
关键词
Synthesis; (chemical);
D O I
10.1039/d4cc03897e
中图分类号
O6 [化学]; TQ03 [化学反应过程]; TQ02 [化工过程(物理过程及物理化学过程)];
学科分类号
0703 ; 081701 ; 081704 ;
摘要
Visible light-induced radical umpolung chemistry is utilized to synthesize trifluoromethylated unnatural α-amino acid and amine derivatives. This approach utilizes photoredox catalysis to perform a single-electron-transfer reduction of imines generating a N-centred radical that eventually migrates to the C-centre followed by a radical-radical cross-coupling to deliver reductive trifluoromethylation products. © 2024 The Royal Society of Chemistry.
引用
收藏
页码:13016 / 13019
相关论文
共 50 条
  • [1] Radical trifluoromethylation via photoredox catalysis
    Nagib, David A.
    MacMillan, David W. C.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [2] Photoredox-Catalyzed Reductive Coupling of Aldehydes, Ketones, and Imines with Visible Light
    Nakajima, Masaki
    Fava, Eleonora
    Loescher, Sebastian
    Jiang, Zhen
    Rueping, Magnus
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (30) : 8828 - 8832
  • [3] Reductive coupling of alkenes with unsaturated imines via a radical pathway
    Qi, Jifeng
    Tang, Haibin
    Chen, Changwei
    Cui, Sunliang
    Xu, Gang
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (15) : 2760 - 2764
  • [4] Photoredox-Catalyzed Multicomponent Synthesis of Functionalized γ-Amino Butyric Acids via Reductive Radical Polar Crossover
    Venditto, Nicholas J.
    Boerth, Jeffrey A.
    ORGANIC LETTERS, 2023, 25 (19) : 3429 - 3434
  • [5] N-Heterocyclic-Carbene-Catalyzed Umpolung of Imines
    Patra, Atanu
    Mukherjee, Subrata
    Das, Tamal Kanti
    Jain, Shailja
    Gonnade, Rajesh G.
    Biju, Akkattu T.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (10) : 2730 - 2734
  • [6] Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis
    Nagib, David A.
    Scott, Mark E.
    MacMillan, David W. C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) : 10875 - +
  • [7] β-Selective Reductive Coupling of Alkenylpyridines with Aldehydes and Imines via Synergistic Lewis Acid/Photoredox Catalysis
    Lee, Katarzyna N.
    Lei, Zhen
    Ngai, Ming-Yu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (14) : 5003 - 5006
  • [8] Allylic C(sp3)-H alkylation via synergistic organo- and photoredox catalyzed radical addition to imines
    Jia, Jiaqi
    Kancherla, Rajesh
    Rueping, Magnus
    Huang, Long
    CHEMICAL SCIENCE, 2020, 11 (19) : 4954 - 4959
  • [9] Reductive Radical Conjugate Addition of Alkyl Electrophiles Catalyzed by a Cobalt/Iridium Photoredox System
    Escobar, Randolph A.
    Johannes, Jeffrey W.
    ORGANIC LETTERS, 2021, 23 (15) : 6046 - 6051
  • [10] Synthesis of Bridged Benzazocines and Benzoxocines by a Titanium-Catalyzed Double-Reductive Umpolung Strategy
    Bichovski, Plamen
    Haas, Thomas M.
    Kratzert, Daniel
    Streuff, Jan
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (06) : 2339 - 2342