Selective Intramolecular C-H Amination through the Metalloradical Activation of Azides: Synthesis of 1,3-Diamines under Neutral and Nonoxidative Conditions

被引：167

作者：

Lu, Hongjian ^{[1
]}

Jiang, Huiling ^{[1
]}

Wojtas, Lukasz ^{[1
]}

Zhang, X. Peter ^{[1
]}

机构：

[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 52期

基金：

美国国家科学基金会;

关键词：

C-H amination; cobalt porphyrins; 1,3-diamines; nitrene transfer; sulfamoyl azides; TRANSITION-METAL-COMPLEXES; ORGANIC AZIDES; EFFICIENT; INSERTION; BONDS; FUNCTIONALIZATION; AZIRIDINATION; AMIDATION; DESIGN; AMINES;

D O I：

10.1002/anie.201005552

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N2 is the only by-product in a stereospecific and highly diastereoselective intramolecular C-H amination of sulfamoyl azides with a cobalt(II)-based metalloradical catalyst (see scheme). The catalytic system has an unusual capacity for the efficient amination of strong primary C-H bonds, as well as secondary and tertiary C-H bonds, and functional-group tolerance is excellent owing to the neutral and nonoxidative conditions. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：10192 / 10196

页数：5

共 50 条

[1] Synthesis of 1,3-Diamines Through Rhodium-Catalyzed C-H Insertion
Kurokawa, Toshiki
Kim, Mihyong
Du Bois, J.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (15) : 2777 - 2779
[2] Selective radical amination of aldehydic C(sp2)-H bonds with fluoroaryl azides via Co( II)-based metalloradical catalysis: synthesis of N-fluoroaryl amides from aldehydes under neutral and nonoxidative conditions
Jin, Li-Mei
Lu, Hongjian
Cui, Yuan
Lizardi, Christopher L.
Arzua, Thiago N.
Wojtas, Lukasz
Cui, Xin
Zhang, X. Peter
CHEMICAL SCIENCE, 2014, 5 (06) : 2422 - 2427
[3] Stereocontrolled concise synthesis of (±)-halosaline through intramolecular C-H amination
Meng, Chun-Yan
Liang, Xiao
Zhang, Hongbin
Wei, Kun
Yang, Yu-Rong
TETRAHEDRON LETTERS, 2019, 60 (27) : 1781 - 1783
[4] Chemoselective intramolecular allylic C-H amination versus C=C aziridination through Co(II)-based metalloradical catalysis
Lu, Hongjian
Jiang, Huiling
Hu, Yang
Wojtas, Lukasz
Zhang, X. Peter
CHEMICAL SCIENCE, 2011, 2 (12) : 2361 - 2366
[5] Selective Synthesis of Osmanaphthalene and Osmanaphthalyne by Intramolecular C-H Activation
Liu, Bin
Xie, Hujun
Wang, Huijuan
Wu, Liqiong
Zhao, Qianyi
Chen, Jinxiang
Wen, Ting Bin
Cao, Zexing
Xia, Haiping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (30) : 5461 - 5464
[6] Synthesis of Differentially Substituted 1,2-Diamines through Advances in C-H Amination Technology
Olson, David E.
Roberts, D. Allen
Du Bois, J.
ORGANIC LETTERS, 2012, 14 (24) : 6174 - 6177
[7] Ruthenium Pybox-Catalyzed Enantioselective Intramolecular C-H Amination of Sulfamoyl Azides en Route to Chiral Vicinal Diamines
Nie, Xin
Yan, Zihan
Ivlev, Sergei
Meggers, Eric
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 750 - 761
[8] Organoselenium-catalyzed synthesis of indoles through intramolecular C-H amination
Zhang, Xuelin
Guo, Ruizhi
Zhao, Xiaodan
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10): : 1334 - 1337
[9] Synthesis of Phenanthridines through Iodine-Supported Intramolecular C-H Amination and Oxidation under Visible Light
Gao, Yan
Jing, Yi
Li, Lixin
Zhang, Jie
Chen, Xuenian
Ma, Yan-Na
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (19): : 12187 - 12198
[10] Ru(II)-Catalyzed Selective C-H Amination of Xanthones and Chromones with Sulfonyl Azides: Synthesis and Anticancer Evaluation
Shin, Youngmi
Han, Sangil
De, Umasankar
Park, Jihye
Sharma, Satyasheel
Mishra, Neeraj Kumar
Lee, Eui-Kyung
Lee, Youngil
Kim, Hyung Sik
Kim, In Su
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19): : 9262 - 9271

← 1 2 3 4 5 →