Copper-catalyzed chemoselective C–H functionalization of quinoxalin-2(1H)-ones with hexafluoroisopropanol

Abstract

An unexpected three-component reaction of quinoxalin-2(1H)-ones, tert-butyl peroxybenzoate (TBPB), and hexafluoroisopropanol (HFIP) is described. Under CuBr-catalyzed and TBPB-oxidized conditions, a variety of hydroxyhexafluoroisobutylated quinoxalin-2(1H)-ones were formed. Furthermore, the first hexafluoroisopropoxylation of the quinoxalin-2(1H)-ones with HFIP is also demonstrated with Cu₂O as the catalyst and PhI(OAc)₂ as the oxidant. These new transformations of HFIP furnish previously unknown and potentially useful fluorinated quinoxalin-2(1H)-one derivatives.