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

20 October 2020, Version 3
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

Electrosynthesis
Silyl Radical Chemistry
Electroreduction
Alkene Functionalization
Allylic substitution
chlorosilanes

Supplementary materials

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