The chemistry of amine radical cations produced by visible light photoredox catalysis

被引:371
作者
Hu, Jie [1 ]
Wang, Jiang [1 ]
Nguyen, Theresa H. [1 ]
Zheng, Nan [1 ]
机构
[1] Univ Arkansas, Dept Chem, Fayetteville, AR 72701 USA
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷
关键词
alpha-amino radical; amine radical cation; catalysis; distonic ion; free radical; iminium ion; photoredox; visible light; C-BOND-CLEAVAGE; PHOTOINDUCED ELECTRON-TRANSFER; TRANSITION-METAL-COMPLEXES; ALPHA-AMINOALKYL RADICALS; PROTON-TRANSFER REACTIONS; DUAL CATALYSIS; H BONDS; COORDINATION-COMPOUNDS; SYNTHETIC APPLICATIONS; COUPLING REACTIONS;
D O I
10.3762/bjoc.9.234
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Amine radical cations are highly useful reactive intermediates in amine synthesis. They have displayed several modes of reactivity leading to some highly sought-after synthetic intermediates including iminium ions, a-amino radicals, and distonic ions. One appealing method to access amine radical cations is through one-electron oxidation of the corresponding amines under visible light photoredox conditions. This approach and subsequent chemistries are emerging as a powerful tool in amine synthesis. This article reviews synthetic applications of amine radical cations produced by visible light photocatalysis.
引用
收藏
页码:1977 / 2001
页数:25
相关论文
共 108 条
  • [51] A Visible-Light-Mediated Oxidative C-N Bond Formation/Aromatization Cascade: Photocatalytic Preparation of N-Arylindoles
    Maity, Soumitra
    Zheng, Nan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (38) : 9562 - 9566
  • [52] 3-METHYL-2,3-DIHYDROBENZOTHIAZOLES AS REDUCING AGENTS - DYE ENHANCED PHOTOREACTIONS
    MASHRAQUI, SH
    KELLOGG, RM
    [J]. TETRAHEDRON LETTERS, 1985, 26 (11) : 1453 - 1456
  • [53] Visible light photooxidative cyclization of amino alcohols to 1,3-oxazines
    Mathis, Cheryl L.
    Gist, Brandi M.
    Frederickson, Conerd K.
    Midkiff, Katie M.
    Marvin, Christopher C.
    [J]. TETRAHEDRON LETTERS, 2013, 54 (16) : 2101 - 2104
  • [54] Discovery of an α-Amino C-H Arylation Reaction Using the Strategy of Accelerated Serendipity
    McNally, Andrew
    Prier, Christopher K.
    MacMillan, David W. C.
    [J]. SCIENCE, 2011, 334 (6059) : 1114 - 1117
  • [55] CHEMICAL APPROACHES TO ARTIFICIAL PHOTOSYNTHESIS
    MEYER, TJ
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (05) : 163 - 170
  • [56] Catalytic oxidation of amines utilizing binuclear copper(II) complex of 7-azaindole
    Minakata, S
    Ohshima, Y
    Takemiya, A
    Ryu, I
    Komatsu, M
    Ohshiro, Y
    [J]. CHEMISTRY LETTERS, 1997, (04) : 311 - 312
  • [57] Direct sp3 C?H Amination of Nitrogen-Containing Benzoheterocycles Mediated by Visible-Light-Photoredox Catalysts
    Miyake, Yoshihiro
    Nakajima, Kazunari
    Nishibayashi, Yoshiaki
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (51) : 16473 - 16477
  • [58] Visible-Light-Mediated Utilization of α-Aminoalkyl Radicals: Addition to Electron-Deficient Alkenes Using Photoredox Catalysts
    Miyake, Yoshihiro
    Nakajima, Kazunari
    Nishibayashi, Yoshiaki
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (07) : 3338 - 3341
  • [59] Synthetic applications of anodic electrochemistry
    Moeller, KD
    [J]. TETRAHEDRON, 2000, 56 (49) : 9527 - 9554
  • [60] Ruthenium catalyzed biomimetic oxidation in organic synthesis inspired by cytochrome P-450
    Murahashi, Shun-Ichi
    Zhang, Dazhi
    [J]. CHEMICAL SOCIETY REVIEWS, 2008, 37 (08) : 1490 - 1501