Towards trans-dual deuterated cyclopropanes via photoredox synergistic deuteration with D2O

Abstract

As the demand for deuterated compounds continues to rise in medicinal chemistry, various methods have been developed to incorporate deuterium atoms. Among these, achieving consecutive trans-dual deuteration remains a challenging task. We have designed a novel strategy to synthesize trans-dual deuterated cyclopropanes at adjacent carbon positions. This approach involves H/D exchange followed by a photocatalyzed deuteroaminomethylation of cyclopropenes, with deuterium oxide serving as the sole deuterium source. The reaction is carried out under mild conditions and exhibits a broad substrate scope, high diastereoselectivity, and promising potential for further applications, making it an attractive transformation for future studies.