Highly C-selective difluoromethylation of β-ketoesters by using TMSCF2Br/lithium hydroxide/N,N,N-trimethylhexadecan-1-ammonium bromide

Jiandong Wang; Etsuko Tokunaga; Norio Shibata

doi:10.1039/C8CC05135F

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Highly C-selective difluoromethylation of β-ketoesters by using TMSCF₂Br/lithium hydroxide/N,N,N-trimethylhexadecan-1-ammonium bromide†

Jiandong Wang,^a Etsuko Tokunaga

^a and Norio Shibata

*^ab

Author affiliations

* Corresponding authors

^a Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-5888, Japan
E-mail: nozshiba@nitech.ac.jp

^b Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, 688 Yingbin Avenue, 321004 Jinhua, China

Abstract

The highly C-selective difluoromethylation of β-ketoesters was achieved by combining TMSCF₂Br/LiOH/N,N,N-trimethylhexadecan-1-ammonium bromide. Compared to other alkali metal salts or organic bases, lithium hydroxide, which served as a difluorocarbene activator from TMSCF₂Br, was crucial in the control of high C/O regioselectivity.

This article is part of the themed collection: Fluorine Chemistry

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Article information

DOI: https://doi.org/10.1039/C8CC05135F
Article type: Communication
Submitted: 27 Jūn. 2018
Accepted: 13 Jūl. 2018
First published: 16 Jūl. 2018

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Chem. Commun., 2018,54, 8881-8884

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Highly C-selective difluoromethylation of β-ketoesters by using TMSCF₂Br/lithium hydroxide/N,N,N-trimethylhexadecan-1-ammonium bromide

J. Wang, E. Tokunaga and N. Shibata, Chem. Commun., 2018, 54, 8881 DOI: 10.1039/C8CC05135F

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Chemical Communications