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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 15期

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

页码：5607 / 5610

页数：4

共 77 条

[31] Direct Construction of Quaternary Carbons from Tertiary Alcohols via Photoredox-Catalyzed Fragmentation of tert-Alkyl N-Phthalimidoyl Oxalates
Lackner, Gregory L.
Quasdorf, Kyle W.
Overman, Larry E.
[J]. 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
Ley, SV
Thomas, AW
[J]. 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
Li, Bi-He
Tian, Shi-Liang
Fang, Zhao
Shi, Zhang-Jie
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (06) : 1115 - 1118
[34] IMIDYL RADICALS
LUNING, U
SKELL, PS
[J]. TETRAHEDRON, 1985, 41 (19) : 4289 - 4302
[35] Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions
Lyons, Thomas W.
Sanford, Melanie S.
[J]. CHEMICAL REVIEWS, 2010, 110 (02) : 1147 - 1169
[36] Copper/Amino Acid Catalyzed Cross-Couplings of Aryl and Vinyl Halides with Nucleophiles
Ma, Dawei
Cai, Qian
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) : 1450 - 1460
[37] Synthesis of biaryls via intermolecular radical addition of heteroaryl and aryl bromides onto arenes
Martínez-Barrasa, V
de Viedma, AG
Burgos, C
Alvarez-Builla, J
[J]. ORGANIC LETTERS, 2000, 2 (24) : 3933 - 3935
[38] Copper-Catalyzed Direct Amination of Electron-Deficient Arenes with Hydroxylamines
Matsuda, Naoki
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
[J]. ORGANIC LETTERS, 2011, 13 (11) : 2860 - 2863
[39] A Graphical Journey of Innovative Organic Architectures That Have Improved Our Lives
McGrath, Nicholas A.
Brichacek, Matthew
Njardarson, Jon T.
[J]. 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
Mei, Tian-Sheng
Wang, Xisheng
Yu, Jin-Quan
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) : 10806 - +

← 1 2 3 4 5 6 7 8 →