Issue 9, 2017
From the journal:

Catalysis Science & Technology

Stereoselective access to trisubstituted fluorinated alkenyl thioethers†

Indira Fabre,ab   Thomas Poisson,c   Xavier Pannecoucke,c   Isabelle Gillaizeau, ORCID logo d   Ilaria Ciofini*b  and  Laurence Grimaud ORCID logo *a  

* Corresponding authors

a PASTEUR, Département de chimie, École normale supérieure, PSL Research University, Sorbonne Universités, UPMC Univ. Paris 06, CNRS, 75005 Paris, France
E-mail: laurence.grimaud@ens.fr

b PSL Research University, Institut de Recherche de Chimie Paris, CNRS Chimie ParisTech, 11 rue P. et M. Curie, 75005 Paris, France
E-mail: ilaria.ciofini@chimie-paristech.fr

c Normandie Univ., INSA Rouen UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France

d Institut de Chimie Organique et Analytique, UMR 7311 CNRS, Université d'Orléans, rue de Chartres, 45067 Orléans cedex 2, France

Abstract

We report the first copper-catalyzed olefinic ethoxy carbonyl difluoromethylation of alkenyl thioethers via direct C–H bond functionalization using BrCF2COOEt. The developed methodology allows the preparation of trisubstituted olefins with a controlled stereochemistry. A mechanistic study is reported and a radical mechanism is revealed.

Graphical abstract: Stereoselective access to trisubstituted fluorinated alkenyl thioethers

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Article information

DOI
https://doi.org/10.1039/C7CY00076F
Article type
Paper
Submitted
13 Jan 2017
Accepted
28 Mar 2017
First published
29 Mar 2017

Catal. Sci. Technol., 2017,7, 1921-1927

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Stereoselective access to trisubstituted fluorinated alkenyl thioethers

I. Fabre, T. Poisson, X. Pannecoucke, I. Gillaizeau, I. Ciofini and L. Grimaud, Catal. Sci. Technol., 2017, 7, 1921 DOI: 10.1039/C7CY00076F

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