Photoredox-Mediated Net-Neutral Radical/Polar Crossover Reactions

被引:146
作者
Wiles, Rebecca J. [1 ]
Molander, Gary A. [1 ]
机构
[1] Univ Penn, Dept Chem, 231 S 34th St, Philadelphia, PA 19104 USA
关键词
photoredox catalysis; radical polar crossover; catalysis; redox-neutral; radical; VISIBLE-LIGHT PHOTOREDOX; C-H FUNCTIONALIZATION; METAL-FREE; CARBOXYLIC-ACIDS; ALKYL-HALIDES; GENERATION; ARYLATION; CATALYSIS; CONSTRUCTION; HETEROARENES;
D O I
10.1002/ijch.201900166
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Radical/Polar Crossover (RPC) chemistry is a rapidly growing subset of photoredox catalysis that is characterized by transformations featuring both radical and ionic modes of reactivity. Net-neutral RPC is particularly interesting in that both the single-electron oxidation and reduction steps occur through interaction with the photocatalyst, thus precluding the need for exogenous oxidants or reductants. As such, these transformations facilitate rapid incorporation of molecular complexity while maintaining mild reaction conditions. This review covers recent advances in photoredox-mediated net-neutral RPC synthetic methods, with a particular emphasis on C-C bond-forming reactions.
引用
收藏
页码:281 / 293
页数:13
相关论文
共 84 条
  • [41] Recent Advances in Photoredox Catalysis Enabled Functionalization of α-Amino Acids and Peptides: Concepts, Strategies and Mechanisms
    Liu, Jian-Quan
    Shatskiy, Andrey
    Matsuura, Bryan S.
    Karkas, Markus D.
    [J]. SYNTHESIS-STUTTGART, 2019, 51 (14): : 2759 - 2791
  • [42] Photoredox-Catalyzed Cyclopropanation of 1,1-Disubstituted Alkenes via Radical-Polar Crossover Process
    Luo, Wenping
    Yang, Yi
    Fang, Yewen
    Zhang, Xinxin
    Jin, Xiaoping
    Zhao, Guicai
    Zhang, Li
    Li, Yan
    Zhou, Wanli
    Xia, Tingting
    Chen, Bin
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (18) : 4215 - 4221
  • [43] Fluoro-artemisinins:: When a gem-difluoroethylene replaces a carbonyl group
    Magueur, Guillaume
    Crousse, Benoit
    Ourevitch, Michle
    Bonnet-Delpon, Danile
    Begue, Jean-Pierre
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (4-5) : 637 - 642
  • [44] Metal-Free Carbonylations by Photoredox Catalysis
    Majek, Michal
    Jacobi von Wangelin, Axel
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (07) : 2270 - 2274
  • [45] Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development
    Matsui, Jennifer K.
    Lang, Simon B.
    Heitz, Drew R.
    Molander, Gary A.
    [J]. ACS CATALYSIS, 2017, 7 (04): : 2563 - 2575
  • [46] Synopsis of Some Recent Tactical Application of Bioisosteres in Drug Design
    Meanwell, Nicholas A.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (08) : 2529 - 2591
  • [47] Alkyl Carbon-Carbon Bond Formation by Nickel/Photoredox Cross-Coupling
    Milligan, John A.
    Phelan, James P.
    Badir, Shorouk O.
    Molander, Gary A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (19) : 6152 - 6163
  • [48] Radical/Polar Annulation Reactions (RPARs) Enable the Modular Construction of Cyclopropanes
    Milligan, John A.
    Phelan, James P.
    Polites, Viktor C.
    Kelly, Christopher B.
    Molander, Gary A.
    [J]. ORGANIC LETTERS, 2018, 20 (21) : 6840 - 6844
  • [49] Recent Advances on Amino Acid Modifications via C-H Functionalization and Decarboxylative Functionalization Strategies
    Mondal, Santanu
    Chowdhury, Sushobhan
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (10) : 1884 - 1912
  • [50] The Prowess of Photogenerated Amine Radical Cations in Cascade Reactions: From Carbocycles to Heterocycles
    Morris, Scott A.
    Wang, Jiang
    Zheng, Nan
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) : 1957 - 1968