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

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.