Ac opper-mediated halotrifluoromethylation of unactivated alkenesusing Umemotos reagent and copper(I) halide (CuX, X = Cl, Br, and I) was developed. TheC uX species (CuI, CuBr, and CuCl) were chosen as the source for bothc opper andh alides because of theirb enchtop stability,c ommercial availability,a nd relatively low cost. Simple exchange of the copper salt provided the desired simultaneous and regioselective incorporation of the halogen atom and of the CF 3 group to various alkenes. This protocol offers an efficienta nd practical route to various b-halotrifluoromethylateda lkanes.F urther modifications of the C À Br bond to C À B, C À Na nd C À Sb onds were performed. These derivatizations show the feasibility of late-stage modifications.
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