Yang Keming, Feng Tian, Qiu Youai
State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China.
Angew Chem Int Ed Engl. 2023 Nov 6;62(45):e202312803. doi: 10.1002/anie.202312803. Epub 2023 Sep 19.
Despite widespread use of the deuterium isotope effect, selective deuterium labeling of chemical molecules remains a major challenge. Herein, a facile and general electrochemically driven, organic mediator enabled deuteration of styrenes with deuterium oxide (D O) as the economical deuterium source was reported. Importantly, this transformation could be suitable for various electron rich styrenes mediated by triphenylphosphine (TPP). The reaction proceeded under mild conditions without transition-metal catalysts, affording the desired products in good yields with excellent D-incorporation (D-inc, up to >99 %). Mechanistic investigations by means of isotope labeling experiments and cyclic voltammetry tests provided sufficient support for this transformation. Notably, this method proved to be a powerful tool for late-stage deuteration of biorelevant compounds.
尽管氘同位素效应已被广泛应用，但化学分子的选择性氘标记仍然是一个重大挑战。在此，报道了一种简便通用的电化学驱动方法，该方法利用有机介质，以氧化氘（D₂O）作为经济的氘源实现了苯乙烯的氘代反应。重要的是，这种转化适用于由三苯基膦（TPP）介导的各种富电子苯乙烯。该反应在温和条件下进行，无需过渡金属催化剂，以良好的产率提供所需产物，且氘掺入率极高（D-inc，高达>99%）。通过同位素标记实验和循环伏安测试进行的机理研究为这种转化提供了充分的支持。值得注意的是，该方法被证明是生物相关化合物后期氘代的有力工具。
