Synthesis of Dichlorocyanomethyl-Functionalized Oxindoles by Cascade Reactions Initiated by Copper(I)-Catalytically Generated Dichlorocyanomethyl Radical

摘要

An efficient and convenient protocol for synthesis of dichlorocyanomethyl-functionalized oxindoles through the cascade reactions of dichlorocyanomethyl radical withN-arylacrylamides is reported. The electrophilic dichlorocyanomethyl radical, which is generated from readily available trichloroacetonitrileviaa copper-catalyzed single-electron transfer (SET) process, undergoes radical addition with the electron-deficient C=C bonds ofN-arylacrylamides, followed by intramolecular cyclization, to provide dichlorocyanomethyl-functionalized oxindoles. No external oxidant is needed in this transformation.