Issue 78, 2018
From the journal:

Chemical Communications

Visible light-promoted umpolung coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines†

Xiao Xu,‡a   Qing-Qiang Min,‡a   Na Lia  and  Feng Liu ORCID logo *ab  

* Corresponding authors

a Jiangsu Key Laboratory of Neuropsychiatric Diseases and Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, People's Republic of China
E-mail: fliu2@suda.edu.cn

b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China

Abstract

Tertiary alcohols bearing a trifluoromethyl group are of considerable medicinal interest. Using an umpolung strategy, we herein report the first intermolecular reductive cross-coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines with the aid of a Brønsted acid catalyst upon visible-light irradiation. This metal-free reaction is operationally simple and performed at ambient temperature, allowing access to desired tertiary alcohols with tri-/difluoromethyl groups in moderate to excellent yields. The commercially available and easily handled Hantzsch ester effectively serves as an electron donor, as well as a hydrogen atom source.

Graphical abstract: Visible light-promoted umpolung coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines

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Article information

DOI
https://doi.org/10.1039/C8CC06748A
Article type
Communication
Submitted
20 Aug 2018
Accepted
06 Sep 2018
First published
07 Sep 2018

Chem. Commun., 2018,54, 11017-11020

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Visible light-promoted umpolung coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines

X. Xu, Q. Min, N. Li and F. Liu, Chem. Commun., 2018, 54, 11017 DOI: 10.1039/C8CC06748A

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