Electroreductive Olefin-Ketone Coupling

27 October 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A user-friendly approach to sidestep the venerable Grignard addition to unactivated ketones to access tertiary alcohols by reversing the polarity of the disconnection. In this work a ketone instead acts as a nucleophile when adding to simple unactivated olefins to accomplish the same overall transformation. The scope of this coupling is broad as enabled using an electrochemical approach and the reaction is scalable, chemoselective, and requires no precaution to exclude air or water. Multiple applications demonstrate the simplifying nature of the reaction on multi-step synthesis and mechanistic studies point to an intuitive mechanism reminiscent of other chemical reductants such as SmI2 (which cannot accomplish the same reaction).

Keywords

Ketyl-Olefin
Ketyl
Electrochemical Grignard
Electrochemical coupling
Reductive coupling

Supplementary materials

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SUPPORTING INFORMATION FINAL
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