N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C-H Amination of Arenes and Heteroarenes

被引:349
作者
Allen, Laura J. [1 ]
Cabrera, Pablo J. [1 ]
Lee, Melissa [1 ]
Sanford, Melanie S. [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
关键词
METAL-FREE CONDITIONS; BOND FORMATION; PHOTOREDOX CATALYSIS; AMBIENT-TEMPERATURE; COUPLING REACTIONS; ORGANIC-SYNTHESIS; IMIDYL RADICALS; PALLADIUM; COPPER; AMIDATION;
D O I
10.1021/ja501906x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This paper reports a room temperature visible light photocatalyzed method for the C-H amination of arenes and heteroarenes. A key enabling advance in this work is the design of N-acyloxyphthalimides as precursors to nitrogen-based radical intermediates for these transformations. A broad substrate scope is presented, including the selective meta-amination of pyridine derivatives. A radical aromatic substitution mechanism is proposed.
引用
收藏
页码:5607 / 5610
页数:4
相关论文
共 77 条
  • [1] ABRAMOVITCH RA, 1989, HETEROCYCLES, V28, P623
  • [2] Organocatalytic, Oxidative, Intramolecular C-H Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature
    Antonchick, Andrey P.
    Samanta, Rajarshi
    Kulikov, Katharina
    Lategahn, Jonas
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) : 8605 - 8608
  • [3] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents
    Beccalli, Egle M.
    Broggini, Gianluigi
    Martinelli, Michela
    Sottocornola, Silvia
    [J]. CHEMICAL REVIEWS, 2007, 107 (11) : 5318 - 5365
  • [4] The Complementary Competitors: Palladium and Copper in C-N Cross-Coupling Reactions
    Beletskaya, Irina P.
    Cheprakov, Andrei V.
    [J]. ORGANOMETALLICS, 2012, 31 (22) : 7753 - 7808
  • [5] Medical implications of benzimidazole derivatives as drugs designed for targeting DNA and DNA associated processes
    Bhattacharya, Santanu
    Chaudhuri, Padmaparna
    [J]. CURRENT MEDICINAL CHEMISTRY, 2008, 15 (18) : 1762 - 1777
  • [6] Pd-Catalyzed Aryl C-H Imidation with Arene as the Limiting Reagent
    Boursalian, Gregory B.
    Ngai, Ming-Yu
    Hojczyk, Katarzyna N.
    Ritter, Tobias
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (36) : 13278 - 13281
  • [7] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines
    Brasche, Gordon
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) : 1932 - 1934
  • [8] RADICAL PHTHALIMIDATION OF AROMATIC-COMPOUNDS BY PHOTOLYSIS OF N-TOSYLOXYPHTHALIMIDE - ROUTE TO PRIMARY AROMATIC-AMINES
    CADOGAN, JIG
    ROWLEY, AG
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (11): : 1069 - 1071
  • [9] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant
    Chen, Xiao
    Hao, Xue-Shi
    Goodhue, Charles E.
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) : 6790 - 6791
  • [10] Visible-Light Photoredox in Homolytic Aromatic Substitution: Direct Arylation of Arenes with Aryl Halides
    Cheng, Yannan
    Gu, Xiangyong
    Li, Pixu
    [J]. ORGANIC LETTERS, 2013, 15 (11) : 2664 - 2667