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

被引:359
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
[31]   Direct Construction of Quaternary Carbons from Tertiary Alcohols via Photoredox-Catalyzed Fragmentation of tert-Alkyl N-Phthalimidoyl Oxalates [J].
Lackner, Gregory L. ;
Quasdorf, Kyle W. ;
Overman, Larry E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (41) :15342-15345
[32]   Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation [J].
Ley, SV ;
Thomas, AW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5400-5449
[33]   Multiple C-H activations to construct biologically active molecules in a process completely free of organohalogen and organometallic components [J].
Li, Bi-He ;
Tian, Shi-Liang ;
Fang, Zhao ;
Shi, Zhang-Jie .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (06) :1115-1118
[34]   IMIDYL RADICALS [J].
LUNING, U ;
SKELL, PS .
TETRAHEDRON, 1985, 41 (19) :4289-4302
[35]   Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions [J].
Lyons, Thomas W. ;
Sanford, Melanie S. .
CHEMICAL REVIEWS, 2010, 110 (02) :1147-1169
[36]   Copper/Amino Acid Catalyzed Cross-Couplings of Aryl and Vinyl Halides with Nucleophiles [J].
Ma, Dawei ;
Cai, Qian .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1450-1460
[37]   Synthesis of biaryls via intermolecular radical addition of heteroaryl and aryl bromides onto arenes [J].
Martínez-Barrasa, V ;
de Viedma, AG ;
Burgos, C ;
Alvarez-Builla, J .
ORGANIC LETTERS, 2000, 2 (24) :3933-3935
[38]   Copper-Catalyzed Direct Amination of Electron-Deficient Arenes with Hydroxylamines [J].
Matsuda, Naoki ;
Hirano, Koji ;
Satoh, Tetsuya ;
Miura, Masahiro .
ORGANIC LETTERS, 2011, 13 (11) :2860-2863
[39]   A Graphical Journey of Innovative Organic Architectures That Have Improved Our Lives [J].
McGrath, Nicholas A. ;
Brichacek, Matthew ;
Njardarson, Jon T. .
JOURNAL OF CHEMICAL EDUCATION, 2010, 87 (12) :1348-1349
[40]   Pd(II)-Catalyzed Amination of C-H Bonds Using Single-Electron or Two-electron Oxidants [J].
Mei, Tian-Sheng ;
Wang, Xisheng ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) :10806-+