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

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

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

Download options Please wait...

Supplementary files

Supplementary information PDF (3209K)

Article information

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

Download Citation

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Chemical Communications