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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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Publication details

The article was received on 10 Jun 2019, accepted on 02 Jul 2019 and first published on 08 Jul 2019


Article type: Edge Article
DOI: 10.1039/C9SC02818H
Chem. Sci., 2019,10, 7340-7344
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    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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