Copper-catalyzed trifluoromethylation of alkenes with an electrophilic trifluoromethylating reagent

Xiao-Ping Wang,Ji-Chang Xiao,Xing Zheng,Jin-Hong Lin,Cheng-Pan Zhang

doi:10.3762/bjoc.9.299

Abstract

An efficient method for the copper-catalyzed trifluoromethylation of terminal alkenes with an electrophilic trifluoromethylating reagent has been developed. The reactions proceeded smoothly to give trifluoromethylated alkenes in good to excellent yields. The results provided a versatile approach for the construction of Cvinyl–CF3 bonds without using prefunctionalized substrates.

Highlights

The incorporation of a trifluoromethyl group into pharmaceutically and agrochemically relevant molecules usually enhances their chemical and metabolic stability, lipophilicity and binding selectivity [1-7]
The past few years has witnessed the rapid advances in transition metal-promoted trifluoromethylation for the construction of Caryl–CF3 bonds [1731]
As part of our continuing interest in trifluoromethylation reactions [25,41-45], we investigated the copper-catalyzed trifluoromethylation of terminal alkenes with electrophilic trifluoromethylating reagents (Scheme 1, reaction 3)

Summary

Introduction

The incorporation of a trifluoromethyl group into pharmaceutically and agrochemically relevant molecules usually enhances their chemical and metabolic stability, lipophilicity and binding selectivity [1-7]. Cho and co-workers reported a radical process for the trifluoromethylation of terminal alkenes without using prefunctionalized substrates, but a volatile reagent was used (Scheme 1, reaction 1) [39]. Szabó described trifluoromethyl-benzoyloxylation of alkynes to construct Cvinyl–CF3 bonds (Scheme 2, reaction 2) [40]. As part of our continuing interest in trifluoromethylation reactions [25,41-45], we investigated the copper-catalyzed trifluoromethylation of terminal alkenes with electrophilic trifluoromethylating reagents (Scheme 1, reaction 3).

Results

Conclusion