Formyl-selective deuteration of aldehydes with D2O via synergistic organic and photoredox catalysis |
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| Authors: | Jianyang Dong Xiaochen Wang Zhen Wang Hongjian Song Yuxiu Liu Qingmin Wang |
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| Institution: | State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071 People''s Republic of China, |
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| Abstract: | Formyl-selective deuteration of aldehydes is of high interest for labeling purposes and for optimizing properties of drug candidates. Herein, we report a mild general method for formyl-selective deuterium labeling of aldehydes with D2O, an inexpensive deuterium source, via a synergistic combination of light-driven, polyoxometalate-facilitated hydrogen atom transfer and thiol catalysis. This highly efficient, scalable reaction showed excellent deuterium incorporation, a broad substrate scope, and excellent functional group tolerance and selectivity and is therefore a practical method for late-stage modification of synthetic intermediates in medicinal chemistry and for generating libraries of deuterated compounds.Formyl-selective deuteration of aldehydes with D2O mediated by the synergistic combination of light-driven, polyoxometalate-facilitated HAT and thiol catalysis is reported. |
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