Domino cyclization/trifluoromethylation of 2-alkynylanilines using fluoroform-derived CuCF3: synthesis of 3-(trifluoromethyl)indoles

Abstract

By employing easily accessible 2-alkynylanilines and the well-established fluoroform-derived CuCF₃ reagent, a novel class of 3-(trifluoromethyl)indoles can be synthesized in good yields with no ambiguity of the CF₃ position. The method utilizes a domino cyclization/trifluoromethylation strategy to construct the indole cores with the concomitant installation of the CF₃ group. The ultimate source of CF₃ is the low-cost industrial by-product fluoroform (CF₃H).