Rh-catalyzed intramolecular sp2 C–H bond difluoromethylenation

Yajun Li; Jiangtao Zhu; Haibo Xie; Shan Li; Dongjie Peng; Zhengke Li; Yongming Wu; Yuefa Gong

doi:10.1039/C2CC30207A

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Rh-catalyzed intramolecular sp² C–H bond difluoromethylenation†

Yajun Li,^ab Jiangtao Zhu,^a Haibo Xie,^a Shan Li,^a Dongjie Peng,^a Zhengke Li,^a Yongming Wu*^a and Yuefa Gong*^b

Author affiliations

* Corresponding authors

^a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
E-mail: ymwu@sioc.ac.cn

^b School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, China
E-mail: gongyf@mail.hust.edu.cn

Abstract

A new Rh-catalyzed intramolecular coupling reaction of a CF₂Br group with a 2-aryl of indole or pyrrolevia C–H bond activation is presented. This reaction represents a new way of incorporating difluoromethylene groups into organic compounds. Preliminary mechanistic studies suggest that this reaction might not occur via a conventional free radical pathway.

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Article information

DOI: https://doi.org/10.1039/C2CC30207A
Article type: Communication
Submitted: 11 Jan 2012
Accepted: 31 Jan 2012
First published: 31 Jan 2012

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Chem. Commun., 2012,48, 3136-3138

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Rh-catalyzed intramolecular sp² C–H bond difluoromethylenation

Y. Li, J. Zhu, H. Xie, S. Li, D. Peng, Z. Li, Y. Wu and Y. Gong, Chem. Commun., 2012, 48, 3136 DOI: 10.1039/C2CC30207A

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Chemical Communications