Visible-light mediated stereospecific C(sp2)–H difluoroalkylation of (Z)-aldoximes

Qian Wang; Haiying Gong; Yifang Zhang; Yi Peng; Hua Chen; Mingjie Li; Hongmei Deng; Jian Hao; Wen Wan

doi:10.1039/D1OB01401C

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Visible-light mediated stereospecific C(sp²)–H difluoroalkylation of (Z)-aldoximes†

Qian Wang,^a Haiying Gong,^a Yifang Zhang,^a Yi Peng,^a Hua Chen,^a Mingjie Li,^a Hongmei Deng,^b Jian Hao

*^a and Wen Wan

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Shanghai University, Shanghai, China
E-mail: wanwen@shu.edu.cn, jhao@shu.edu.cn

^b Laboratory of Microstructures, Shanghai University, China

Abstract

A visible light mediated stereospecific C(sp²)–H difluoroalkylation of (Z)-aldoximes to (E)-difluoroalkylated ketoximes has been described. In this reaction, (hetero)-aromatic and aliphatic difluoroalkylated ketoximes could be obtained with the retention of the configuration of the starting aldoximes. A preliminary mechanism study showed that a difluoromethyl radical via an SET pathway was involved.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D1OB01401C
Article type: Paper
Submitted: 19 Jul 2021
Accepted: 26 Aug 2021
First published: 27 Aug 2021

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Org. Biomol. Chem., 2021,19, 7867-7874

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Visible-light mediated stereospecific C(sp²)–H difluoroalkylation of (Z)-aldoximes

Q. Wang, H. Gong, Y. Zhang, Y. Peng, H. Chen, M. Li, H. Deng, J. Hao and W. Wan, Org. Biomol. Chem., 2021, 19, 7867 DOI: 10.1039/D1OB01401C

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Organic & Biomolecular Chemistry