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

Lei Liu; Zhao Zhang; Yucheng Wang; Yan Zhang; Jie Li

doi:10.1055/s-0039-1690087

Synthesis, Table of Contents

Synthesis 2020; 52(24): 3881-3890
DOI: 10.1055/s-0039-1690087

paper

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

Lei Liu ‡

^aSchool of Pharmaceutical Sciences, Jiangnan University, Lihu Road 1800, 214122 Wuxi, Jiangsu, P. R. of China Email: jjackli@jiangnan.edu.cn

,

Zhao Zhang ‡

^aSchool of Pharmaceutical Sciences, Jiangnan University, Lihu Road 1800, 214122 Wuxi, Jiangsu, P. R. of China Email: jjackli@jiangnan.edu.cn

,

Yucheng Wang ‡

^aSchool of Pharmaceutical Sciences, Jiangnan University, Lihu Road 1800, 214122 Wuxi, Jiangsu, P. R. of China Email: jjackli@jiangnan.edu.cn

,

Yan Zhang

^aSchool of Pharmaceutical Sciences, Jiangnan University, Lihu Road 1800, 214122 Wuxi, Jiangsu, P. R. of China Email: jjackli@jiangnan.edu.cn

,

Jie Li ∗

^aSchool of Pharmaceutical Sciences, Jiangnan University, Lihu Road 1800, 214122 Wuxi, Jiangsu, P. R. of China Email: jjackli@jiangnan.edu.cn

^bKey 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

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Abstract

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‡ 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.

Key words

C(sp³)–H activation - electrophilic amination - cobalt(III) catalysis - anthranils - thioamides

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References

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