Visible-light-mediated deuteration of silanes with deuterium oxide.
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2019
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Abstract
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-light-mediated metal-free deuteration of silanes using DO 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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zhou2019visiblelightmediatedchemical
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| Authors | Zhou, Rong;Li, Jiesheng;Cheo, Han Wen;Chua, Rachel;Zhan, Gu;Hou, Zhaomin;Wu, Jie; |
| Journal | Chemical science |
| Year | 2019 |
| DOI |
10.1039/c9sc02818h
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