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An Electroreductive Approach to Silyl Radical Chemistry via Strong Si–Cl Bond Activation

preprint
revised on 19.10.2020 and posted on 20.10.2020 by Lingxiang Lu, Juno Siu, Yihuan Lai, Song Lin
The construction of C(sp3)–Si bonds is important in synthetic, medicinal, and materials chemistry. In this context, reactions mediated by silyl radicals have become increasingly attractive but methods for accessing these intermediates remain limited. We present a new strategy for silyl radical generation via electroreduction of readily available chlorosilanes. At highly biased potentials, electrochemistry grants access to silyl radicals through energetically uphill reductive cleavage of strong Si–Cl bonds. This strategy proved to be general in various alkene silylation reactions including disilylation, hydrosilylation, and allylic silylation under simple and transition-metal-free conditions.

Funding

An electrocatalytic approach to discovering new synthetic transformations

National Institute of General Medical Sciences

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History

Email Address of Submitting Author

songlin@cornell.edu

Institution

Cornell University

Country

United States

ORCID For Submitting Author

0000-0002-8880-6476

Declaration of Conflict of Interest

No conflict of interest

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