| Literature DB >> 33259715 |
Pengfei Hu1,2, Byron K Peters1,2, Christian A Malapit3,2, Julien C Vantourout1,2, Pan Wang4, Jinjun Li4, Lucas Mele5, Pierre-Georges Echeverria5, Shelley D Minteer3,2, Phil S Baran1,2.
Abstract
A user-friendly approach is presented 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 multistep synthesis, and mechanistic studies point to an intuitive mechanism reminiscent of other chemical reductants such as SmI2 (which cannot accomplish the same reaction).Entities:
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Year: 2020 PMID： 33259715 PMCID： PMC8353665 DOI： 10.1021/jacs.0c11214
Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419