Affiliation:
1. 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
Abstract
AbstractDespite 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 (D2O) 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.
Funder
National Key Research and Development Program of China
National Natural Science Foundation of China