Comprehensive Study and Development of a Metal‐Free and Mild Nucleophilic Trifluoromethoxylation

Author:

Bonnefoy Clémence1ORCID,Panossian Armen2ORCID,Hanquet Gilles2ORCID,Leroux Frédéric R.2ORCID,Toulgoat Fabien13ORCID,Billard Thierry1ORCID

Affiliation:

1. Institute of Chemistry and Biochemistry (ICBMS – UMR CNRS 5246) Univ Lyon CNRS, Université Lyon 1 CPE Lyon 1 rue Victor Grignard 69622 Lyon France

2. Université de Strasbourg Université de Haute-Alsace CNRS, UMR 7042-LIMA, ECPM 67000 Strasbourg France

3. CPE Lyon Campus LyonTech-La Doua 43 Bd du 11 novembre 1918 69616 Villeurbanne France

Abstract

AbstractAmong the general interest in fluorinated compounds, trifluoromethoxylated molecules play a specific role. However, despite this interest, the development of efficient reagents to perform trifluoromethoxylation reactions remains a challenge. Here, 2,4‐dinitro‐trifluoromethoxybenzene (DNTFB) is used as a trifluoromethoxylating reagent to perform nucleophilic substitution under mild metal‐free conditions with different leaving groups, including direct dehydroxytrifluoromethoxylation. A mechanistic study rationalized the reaction and subsequently proposed only three reaction conditions, depending on the reactivity of the starting substrates.

Funder

Agence Nationale de la Recherche

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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