Copper-catalyzed chemoselective C–H functionalization of quinoxalin-2(1<i>H</i>)-ones with hexafluoroisopropanol
Hai‐Yan Su, Xiaolei Zhu, Yangen Huang, Xiu‐Hua Xu, Feng‐Ling Qing
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.
Topics & Concepts
Surface modificationCatalysisCopperChemistryCombinatorial chemistryMedicinal chemistryPolymer chemistryOrganic chemistryPhysical chemistryFluorine in Organic ChemistrySynthesis and Biological EvaluationCyclopropane Reaction Mechanisms