Progress in copper-catalyzed trifluoromethylation.

Guan-Bao Li,Chun Song,Chao Zhang,Yu-Dao Ma

doi:10.3762/bjoc.14.11

Abstract

The introduction of trifluoromethyl groups into organic molecules has attracted great attention in the past five years. In this review, we describe the recent efforts in the development of trifluoromethylation via copper catalysis using nucleophilic, electrophilic or radical trifluoromethylation reagents.

Highlights

The fluorine atom has a strong electronegativity and a small atomic radius, and the incorporation of fluoroalkyl groups into molecules imparts a variety of features
Organic molecules bearing trifluoromethyl groups are widely used in pharmaceuticals and agrochemicals, such as the antidepressant fluoxetine, the anti-ulcer drug lansoprazole and so on (Figure 1)
The specific roles of the trifluoromethyl group (CF3) in biologically active molecules promote the development of novel methods to construct C–CF3 bonds in the past few years

Summary

Introduction

The fluorine atom has a strong electronegativity and a small atomic radius, and the incorporation of fluoroalkyl groups into molecules imparts a variety of features. Scheme 2: Addition of a Lewis acid into copper-catalyzed trifluoromethylation of aryl iodides and the proposed mechanism. Difluorocarbene and fluoride combined into a CF3 species in the presence of Cu2+ and Cu. In contrast with the majority of previously reported copper-mediated trifluoromethylation reactions of haloarenes, CuCF3 generated in situ without any ligand reacts with the haloarenes to provide the corresponding products in good to excellent yields with good functional group compatibility.

Results

Conclusion