Oximinotrifluoromethylation of unactivated alkenes under ambient conditions

Na Wang; Jian Wang; Yu-Long Guo; Lei Li; Yan Sun; Zhuang Li; Hong-Xia Zhang; Zhen Guo; Zhong-Liang Li; Xin-Yuan Liu

doi:10.1039/C8CC05186K

Oximinotrifluoromethylation of unactivated alkenes under ambient conditions†

Na Wang,‡^ab Jian Wang,‡^b Yu-Long Guo,^b Lei Li,^b Yan Sun,^b Zhuang Li,^b Hong-Xia Zhang,^a Zhen Guo,

^a Zhong-Liang Li*^c and Xin-Yuan Liu

*^b

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* Corresponding authors

^a College of Materials Science & Engineering, Key Laboratory of Interface Science and Engineering in Advanced Materials, Ministry of Education, Taiyuan University of Technology, Shanxi, China

^b Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518055, China
E-mail: liuxy3@sustc.edu.cn

^c Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen, China
E-mail: lizl@sustc.edu.cn

Abstract

An efficient protocol for oximinotrifluoromethylation of unactivated alkenes was developed via trifluoromethyl radical-induced intramolecular remote oximino migration under mild reaction conditions, providing a wide range of β-trifluoromethylated oximes. Other fluoroalkyl radicals were also applicable for this transformation. This method provided access to synthetically challenging medium-sized ring scaffolds and the 6,7,5-fused lactam skeleton.

This article is part of the themed collection: Fluorine Chemistry

Chemical Communications

Oximinotrifluoromethylation of unactivated alkenes under ambient conditions†

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