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Electroreductive Olefin-Ketone Coupling

preprint
submitted on 24.10.2020, 22:40 and posted on 27.10.2020, 11:07 by Pengfei Hu, Byron Peters, Christian A. Malapit, Julien Vantourout, Pan Wang, Jinjun Li, Lucas Mele, Pierre-Georges Echeverria, Shelley D. Minteer, Phil Baran

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).

Funding

NIH (GM-118176)

NSF (CCI Phase I grant 1740656)

NSF (Phase II grant 2002158)

History

Email Address of Submitting Author

pbaran@scripps.edu

Institution

Scripps Research

Country

USA

ORCID For Submitting Author

0000-0001-9193-9053

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Version 1.0

Exports