期刊
CHEMICAL SCIENCE
卷 10, 期 31, 页码 7340-7344出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc02818h
关键词
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资金
- Ministry of Education (MOE) of Singapore [MOE2017-T2-2-081]
- GSK-EDB [R-143-000-687-592]
- National Natural Science Foundation of China [21702142, 21871205]
- Japan Society for the Promotion of Science [26220802]
Isotopically labeled compounds are highly desirable as they can serve as both mechanistic probes in chemistry and diagnostic tools in medicinal research. Herein, we report an unprecedented visible-lightmediated metal-free deuteration of silanes using D2O as an inexpensive, readily available, and easy to handle deuterium source. A broad range of aryl-and alkyl-substituted silanes were deuterated with high deuterium incorporations and yields. Furthermore, a 100 gram-scale synthesis was demonstrated using continuous-flow micro-tubing reactors, where enhanced reaction efficiency was obtained. The photoredox-catalyzed polarity matched hydrogen atom transfer (HAT) between silanes and the thiol HAT catalyst was responsible for the efficient deuteration.
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