This review highlights the recent advances in utilizing epoxides as alkylating reagents in transition-metal-catalyzed C−H alkylation, along with its associated synthetic applications in organic synthesis.

Abstract

The alkylation of arenes is one of the most fundamental transformations in synthetic chemistry and the transition-metal-catalyzed direct C−H alkylation represents a straightforward and attractive approach from both atom and step-economy perspectives. Epoxides, the smallest three-membered saturated O-heterocycles that can be easily prepared in racemic or enantioenriched forms, are highly useful building blocks for the synthesis of complex organic molecules. Owing to their inherent high ring-strain, epoxides readily undergo ring-opening reactions and have been used as alkylating reagents for C−H alkylation catalyzed by transition metals. This review summarizes recent advances in utilizing epoxides as alkylating reagents in transition-metal-catalyzed C−H alkylation as well as their synthetic applications in organic synthesis.