Rhodium-Catalyzed Direct ortho C-N Bond Formation of Aromatic Azo Compounds with Azides

被引：78

作者：

Wang, Hao ^{[1
]}

Yu, Yang ^{[1
]}

Hong, Xiaohu ^{[1
]}

Tan, Qitao ^{[1
]}

Xu, Bin ^{[1
,2
,3
]}

机构：

[1] Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[3] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 07期

基金：

中国国家自然科学基金;

关键词：

DECARBOXYLATIVE ORTHO-ACYLATION; H AMIDATION; DIRECT ACCESS; AMINATION; ARENES; AZOBENZENES; FUNCTIONALIZATION; SULFONYL; AZOARENES; ANILINES;

D O I：

10.1021/jo500412w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient rhodium-catalyzed regioselective C-N bond formation of azo compounds in good to excellent yields through C-H bond functionalization using azides as the nitrogen source was developed. Alkyl, aryl, and sulfonyl azides could be efficiently assembled in this reaction with excellent functional group tolerance.

引用

页码：3279 / 3288

页数：10

共 50 条

[1] Rhodium-Catalyzed Direct C-H Amidation of Azobenzenes with Sulfonyl Azides: A Synthetic Route to Sterically Hindered ortho-Substituted Aromatic Azo Compounds
Jia, Xuefeng
Han, Jie
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09): : 4180 - 4185
[2] Rhodium-Catalyzed Transarylation of Benzamides: C-C Bond vs C-N Bond Activation
Long, Yang
Su, Zhishan
Zheng, Yanling
He, Shiyu
Zhong, Jing
Xiang, Haifeng
Zhou, Xiangge
ACS CATALYSIS, 2020, 10 (05): : 3398 - 3403
[3] Rhodium-Catalyzed C-B Bond Formation
Cuenca, Ana B.
Fernandez, Elena
RHODIUM CATALYSIS, 2018, 61 : 1 - 29
[4] Rhodium-Catalyzed Direct Oxidative Carbonylation of Aromatic C-H Bond with CO and Alcohols
Guan, Zheng-Hui
Ren, Zhi-Hui
Spinella, Stephen M.
Yu, Shichao
Liang, Yong-Min
Zhang, Xumu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (02) : 729 - 733
[5] Rhodium-Catalyzed C-H Bond Functionalization with Amides by Double C-H/C-N Bond Activation
Meng, Guangrong
Szostak, Michal
ORGANIC LETTERS, 2016, 18 (04) : 796 - 799
[6] Ruthenium- and rhodium-catalyzed direct carbonylation of the ortho C-H bond in the benzene ring of N-arylpyrazoles
Asaumi, T
Matsuo, T
Fukuyama, T
Ie, Y
Kakiuchi, F
Chatani, N
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (13): : 4433 - 4440
[7] Rhodium-Catalyzed Synthesis of 2-Methylindoles via C-N Bond Cleavage of N-Allylbenzimidazole
Biswal, Pragati
Nanda, Tanmayee
Prusty, Namrata
Mohanty, Smruti Ranjan
Ravikumar, Ponneri C.
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13): : 7988 - 7997
[8] Rhodium-catalyzed ortho-alkylation of aromatic aldimines and ketimines via C-H bond activation
Lim, YG
Han, JS
Yang, SS
Chun, JH
TETRAHEDRON LETTERS, 2001, 42 (29) : 4853 - 4856
[9] Rhodium-Catalyzed Direct ortho-Arylation of Anilines
Jacob, Clement
Annibaletto, Julien
Peng, Ju
Bai, Ruopeng
Maes, Bert U. W.
Lan, Yu
Evano, Gwilherm
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (30)
[10] Regioselective Ortho Olefination of Aryl Sulfonamide via Rhodium-Catalyzed Direct C-H Bond Activation
Xie, Weijia
Yang, Jie
Wang, Baiquan
Li, Bin
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17): : 8278 - 8287

← 1 2 3 4 5 →