Synthesis 2020; 52(24): 3881-3890
DOI: 10.1055/s-0039-1690087
paper
© Georg Thieme Verlag Stuttgart · New York

Electrophilic Amination with Anthranils through Thioamide-Assisted Cobalt(III)-Catalyzed C(sp3)–H Activation

Lei Liu ‡
a   School of Pharmaceutical Sciences, Jiangnan University, Lihu Road 1800, 214122 Wuxi, Jiangsu, P. R. of China   Email: jjackli@jiangnan.edu.cn
,
Zhao Zhang ‡
a   School of Pharmaceutical Sciences, Jiangnan University, Lihu Road 1800, 214122 Wuxi, Jiangsu, P. R. of China   Email: jjackli@jiangnan.edu.cn
,
Yucheng Wang ‡
a   School of Pharmaceutical Sciences, Jiangnan University, Lihu Road 1800, 214122 Wuxi, Jiangsu, P. R. of China   Email: jjackli@jiangnan.edu.cn
,
Yan Zhang
a   School of Pharmaceutical Sciences, Jiangnan University, Lihu Road 1800, 214122 Wuxi, Jiangsu, P. R. of China   Email: jjackli@jiangnan.edu.cn
,
Jie Li
a   School of Pharmaceutical Sciences, Jiangnan University, Lihu Road 1800, 214122 Wuxi, Jiangsu, P. R. of China   Email: jjackli@jiangnan.edu.cn
b   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Ren-Ai Road 199, 215123 Suzhou, Jiangsu, P. R. of China
› Author Affiliations
This work was supported by the National Natural Science Foundation of China (Grant No. 21602083) and the Natural Science Foundation of Jiangsu Province (Grant No. BK20160160). We also thank the Fundamental Research Funds for the Central Universities (JUSRP51703A) and Soochow University.
Further Information

Publication History

Received: 04 January 2020

Accepted after revision: 13 February 2020

Publication Date:
03 March 2020 (online)


‡ These authors contributed equally to this work.

Abstract

Cobalt(III)-catalyzed electrophilic amination of inert C(sp3)–H bonds of weakly coordinating thioamides with readily accessible anthranil derivatives was accomplished under mild conditions, with good functional group tolerance, thus providing various amino aldehydes and amino ketones. Moreover, our protocol with the versatile [Cp*Co(MeCN)3][SbF6]2 features excellent atom-economy and oxidant-free conditions, and allows facile late-stage functionalization.

Supporting Information