Electrochemical Reductive Functionalization of Alkenes with Deuterochloroform as a One-Carbon Deuteration Block

Deuterochloroform is the most common organic deuterated solvent. However, the synthetic chemistry of deuterochloroform has been marginally explored because of its intrinsic limitations, including elimination and scrambling. In this work, an electrochemical protocol was developed to use deuterochloroform as a one-carbon deuteration block in the cyclopropanation and hydrochloromethylation of alkenes. By employing different reaction conditions, the chemoselectivity could be regulated to give divergent products. Typically, deuterium incorporation above 93% to 99% could be achieved.