Intramolecular, Site-Selective, Iodine-Mediated, Amination of Unactivated (sp³)C-H Bonds for the Synthesis of Indoline Derivatives

Jinguo Long, Xin Cao, Longzhi Zhu, Renhua Qiu, Chak-Tong Au, Shuang-Feng Yin, Takanori Iwasaki and Nobuaki Kambe

*State Key Laboratory of Chemo/Biosensing and Chemometrics,College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, China, Email: renhuaqiuhnu.edu.cn, sf_yinhnu.edu.cn

J. Long, X. Cao, L. Zhu, R. Qiu, C.-T. Au, S.-F. Yin, T. Iwasaki, N. Kambe, Org. Lett., 2017, 19, 2793-2796.

DOI: 10.1021/acs.orglett.7b00846

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Abstract

A transition-metal-free, iodine-mediated oxidative intramolecular amination of anilines provides indolines via cleavage of unactivated (sp³)C-H and N-H bonds. The reaction could be performed on a gram scale for the synthesis of functionalized indolines.

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proposed mechanism

Key Words

indolines, iodine, DTBP

ID: J54-Y2017

Intramolecular, Site-Selective, Iodine-Mediated, Amination of Unactivated (sp3)C-H Bonds for the Synthesis of Indoline Derivatives

Jinguo Long, Xin Cao, Longzhi Zhu, Renhua Qiu*, Chak-Tong Au, Shuang-Feng Yin*, Takanori Iwasaki and Nobuaki Kambe

Intramolecular, Site-Selective, Iodine-Mediated, Amination of Unactivated (sp³)C-H Bonds for the Synthesis of Indoline Derivatives

Jinguo Long, Xin Cao, Longzhi Zhu, Renhua Qiu, Chak-Tong Au, Shuang-Feng Yin, Takanori Iwasaki and Nobuaki Kambe