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Issue 31, 2019
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Visible-light-mediated deuteration of silanes with deuterium oxide

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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 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.

Graphical abstract: Visible-light-mediated deuteration of silanes with deuterium oxide

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Supplementary files

Article information


Submitted
10 Jun 2019
Accepted
02 Jul 2019
First published
08 Jul 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 7340-7344
Article type
Edge Article

Visible-light-mediated deuteration of silanes with deuterium oxide

R. Zhou, J. Li, H. W. Cheo, R. Chua, G. Zhan, Z. Hou and J. Wu, Chem. Sci., 2019, 10, 7340
DOI: 10.1039/C9SC02818H

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