Regioselective C(sp3)–H fluorination of ketones: from methyl to the monofluoromethyl group

Qiu-Zi Wu; Yang-Jie Mao; Kun Zhou; Hong-Yan Hao; Lei Chen; Shuang Wang; Zhen-Yuan Xu; Shao-Jie Lou; Dan-Qian Xu

doi:10.1039/D0CC07093A

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Regioselective C(sp³)–H fluorination of ketones: from methyl to the monofluoromethyl group†

Qiu-Zi Wu,^a Yang-Jie Mao,

^a Kun Zhou,^a Hong-Yan Hao,^a Lei Chen,^a Shuang Wang,^a Zhen-Yuan Xu,^a Shao-Jie Lou

*^a and Dan-Qian Xu

*^a

Author affiliations

* Corresponding authors

^a Catalytic Hydrogenation Research Center, State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Key Laboratory of Green Pesticides and Cleaner Production Technology of Zhejiang Province, Zhejiang University of Technology, Hangzhou 310014, P. R. China
E-mail: chrc@zjut.edu.cn, loushaojie@zjut.edu.cn

Abstract

Herein, we report a novel strategy to access CH₂F-containing ketones through Pd-catalysed β-selective methyl C(sp³)–H fluorination. The reaction features high regioselectivity and a broad substrate scope, constituting a modular method for the late-stage transformation of the native methyl (CH₃) into the monofluoromethyl (CH₂F) group.

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Article information

DOI: https://doi.org/10.1039/D0CC07093A
Article type: Communication
Submitted: 26 Oct 2020
Accepted: 14 Dec 2020
First published: 15 Dec 2020

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Chem. Commun., 2021,57, 765-768

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Regioselective C(sp³)–H fluorination of ketones: from methyl to the monofluoromethyl group

Q. Wu, Y. Mao, K. Zhou, H. Hao, L. Chen, S. Wang, Z. Xu, S. Lou and D. Xu, Chem. Commun., 2021, 57, 765 DOI: 10.1039/D0CC07093A

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Chemical Communications