With the fast development of synthetic chemistry, the introduction of functional group into organic molecules has attracted increasing attention. In these reactions, the difunctionalization of unsaturated bonds, traditionally with one nucleophile and one electrophile, is a powerful strategy for the chemical synthesis. In this work, we develop a different path of electrochemical oxidative difunctionalization of diazo compounds with two different nucleophiles. Under metal-free and external oxidant-free conditions, a series of structurally diverse heteroatom-containing compounds hardly synthesized by traditional methods (such as high-value alkoxy-substituted phenylthioacetates, α-thio, α-amino acid derivatives as well as α-amino, β-amino acid derivatives) are obtained in synthetically useful yields. In addition, the procedure exhibits mild reaction conditions, excellent functional-group tolerance and good efficiency on large-scale synthesis. Importantly, the protocol is also amenable to the key intermediate of bioactive molecules in a simple and practical process.

随着合成化学的快速发展，在有机分子中引入官能团越来越受到人们的关注。在这些反应中，不饱和键的双官能化（传统上使用一个亲核试剂和一个亲电试剂）是化学合成的有力策略。在这项工作中，我们开发了具有两种不同亲核试剂的重氮化合物电化学氧化双官能化的不同途径。在无金属、无外部氧化剂的条件下，传统方法难以合成一系列结构多样的含杂原子化合物（如高价值的烷氧基取代苯硫代乙酸酯、α-硫代、α-氨基酸衍生物以及α-氨基，β-氨基酸衍生物）以合成有用的产率获得。此外，该程序还具有温和的反应条件、优异的官能团耐受性和良好的大规模合成效率。重要的是，该协议还适用于简单实用的过程中生物活性分子的关键中间体。