Catalyst‐Free Thia‐Michael Addition to α‐Trifluoromethylacrylates for 3D Network Synthesis

Author:

Berne Dimitri1ORCID,Lemouzy Sébastien1ORCID,Guiffrey Pascale1,Caillol Sylvain1ORCID,Ladmiral Vincent1ORCID,Manoury Eric2ORCID,Poli Rinaldo23ORCID,Leclerc Eric1ORCID

Affiliation:

1. ICGM Univ Montpellier, CNRS, ENSCM Montpellier France

2. CNRS LCC (Laboratoire de Chimie de Coordination) UPS INPT Université de Toulouse 205 route de Narbonne 31077 Toulouse, Cedex 4 France

3. Institut Universitaire de France 1, rue Descartes 75231 Paris France

Abstract

AbstractThia‐Michael additions (1,4‐additions of a thiol to a Michael acceptor) are generally catalyzed by an external Brønsted or Lewis base. A spontaneous (uncatalyzed) Michael addition of thiols to α‐trifluoromethyl acrylates is described, as well as its application to the very efficient preparation of a thermoset. A thorough mechanistic investigation, based on an experimental kinetic study and on DFT calculations, is presented for the addition of arene‐ and alkanethiols to tert‐butyl trifluoromethyl acrylate in polar aprotic solvents, unveiling a probable solvent‐assisted proton transfer in the rate‐determining step and a considerable lowering of the energy barrier induced by the CF3 group.

Funder

Agence Nationale de la Recherche

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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