Towards trans-dual deuterated cyclopropanes via photoredox synergistic deuteration with D(2)O

利用光氧化还原协同氘代反应与D(2)O反应合成反式双氘代环丙烷

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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.

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