Rhodium-Catalyzed Transarylation of Benzamides: C-C Bond vs C-N Bond Activation

被引：27

作者：

Long, Yang ^{[1
]}

Su, Zhishan ^{[1
]}

Zheng, Yanling ^{[1
]}

He, Shiyu ^{[1
]}

Zhong, Jing ^{[1
]}

Xiang, Haifeng ^{[1
]}

Zhou, Xiangge ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Chengdu 610064, Peoples R China

来源：

ACS CATALYSIS | 2020年 / 10卷 / 05期

基金：

中国国家自然科学基金;

关键词：

amide; C-C activation; C-H activation; arylation; rhodium catalysis; DFT; CARBON-CARBON BONDS; TWISTED AMIDES; CLEAVAGE; REDUCTION; ACIDS;

D O I：

10.1021/acscatal.9b05214

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A rhodium-catalyzed transarylation of benzamides via selective C-C bond activation with arylboronic acids was described, which was distinct from the conventional metal-catalyzed C-N bond activation. This transformation exhibited good functional group compatibility with yields up to 88%, offering a practical approach for the construction and functionalization of benzamides. Preliminary experimental and computational studies revealed the selectivity of metal insertion into the C-C bond or the C-N bond was greatly affected by substituents on the amide's N atom.

引用

页码：3398 / 3403

页数：11

共 50 条

[1] Rhodium-catalyzed activation and functionalization of the C-C bond of biphenylene
Iverson, CN
Jones, WD
[J]. ORGANOMETALLICS, 2001, 20 (26) : 5745 - 5750
[2] Enantioselective Rhodium-catalyzed C-C Bond Activation of Cyclobutanones
Souillart, Laetitia
Cramer, Nicolai
[J]. CHIMIA, 2015, 69 (04) : 187 - 190
[3] Enantioselective Rhodium-Catalyzed C-C Bond Activations
Seiser, Tobias
Cramer, Nicolai
[J]. CHIMIA, 2010, 64 (03) : 153 - 156
[4] Rhodium-catalyzed C-C bond cleavage reactions
Necas, David
Kotora, Martin
[J]. CURRENT ORGANIC CHEMISTRY, 2007, 11 (17) : 1566 - 1591
[5] Rhodium-Catalyzed C-H Bond Functionalization with Amides by Double C-H/C-N Bond Activation
Meng, Guangrong
Szostak, Michal
[J]. ORGANIC LETTERS, 2016, 18 (04) : 796 - 799
[6] Rhodium-catalyzed C-C Bond Cleavage Reactions - An Update
Korotvicka, Ales
Necas, David
Kotora, Martin
[J]. CURRENT ORGANIC CHEMISTRY, 2012, 16 (10) : 1170 - 1214
[7] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation
Colby, Denise A.
Bergman, Robert G.
Ellman, Jonathan A.
[J]. CHEMICAL REVIEWS, 2010, 110 (02) : 624 - 655
[8] Iron-Catalyzed C-C Bond Cleavage and C-N Bond Formation
Li, Wenjuan
Zheng, Xiaojian
Li, Zhiping
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) : 181 - 190
[9] Lactone formation by rhodium-catalyzed C-C bond cleavage of cyclobutanone
Murakami, M
Tsuruta, T
Ito, Y
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (14) : 2484 - +
[10] Rhodium-catalyzed alkenylation of allylbenzenes via C-C bond cleavage
Kakiuchi, Fumitoshi
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257

← 1 2 3 4 5 →