Dichloromethane as a C1 Synthon for Copper-Catalyzed Dual Functionalization of Olefins.

A novel copper-catalyzed difunctionalization of alkenes with dichloromethane as a C1 synthon has been established. This method efficiently constructs C-C bonds via concomitant methylene insertion and chloroalkyl functionalization, providing a direct and modular approach for the synthesis of noncyclic alkyl chloride products using simple and readily available starting materials. The practicability of this new approach has been successfully applied at the gram scale. Moreover, this methodology extends to the synthesis of deuterium-labeling alkyl chloride products, highlighting its potential for isotopic labeling and its versatility in organic synthesis and drug discovery.