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Electrochemical Reductive Functionalization of Alkenes with Deuterochloroform as a One-Carbon Deuteration Block
Xiaofeng Zhang1, Xu Cheng1,2
1School of Chemistry and Chemical Engineering, Nanjing University, Xianlin Road 163, Qixia District, Nanjing 210023, China.
Abstract:
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.
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