Synthesis of gem-Difluoro Olefins through C−H Functionalization and β-fluoride Elimination Reactions

Abstract

A palladium catalyzed C−H functionalization and consecutive β-fluoride elimination reaction between indole heterocycles and fluorinated diazoalkanes is reported. This approach provides for the first time a facile method for the rapid synthesis of gem-difluoro olefins using fluorinated diazoalkanes under mild reaction conditions. Cyclopropanation products were obtained when N-arylated rather than N-alkylated indoles were applied in this reaction. Mechanistic studies reveal the importance of the β-fluoride elimination step in this transformation. This method presents a new concept for the simple and direct transfer of a 1-aryl-(2,2-difluorovinyl) group to access gem-difluoro olefins.