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Electrochemical Deconstructive Functionalization of Cycloalkanols via Alkoxy Radicals Enabled by Proton-Coupled Electron Transfer.

ABSTRACT: Herein, we report a new electrochemical method for alkoxy radical generation from alcohols using a proton-coupled electron transfer (PCET) approach, showcased via the deconstructive functionalization of cycloalkanols. The electrochemical method is applicable across a diverse array of substituted cycloalkanols, accessing a broad range of synthetically useful distally functionalized ketones. The orthogonal derivatization of the products has been demonstrated through chemoselective transformations, and the electrochemical process has been performed on a gram scale in continuous single-pass flow.

SUBMITTER: Hareram MD

PROVIDER: S-EPMC9171832 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Electrochemical Deconstructive Functionalization of Cycloalkanols via Alkoxy Radicals Enabled by Proton-Coupled Electron Transfer.

Hareram Mishra Deepak MD El Gehani Albara A M A AAMA Harnedy James J Seastram Alex C AC Jones Andrew C AC Burns Matthew M Wirth Thomas T Browne Duncan L DL Morrill Louis C LC

Organic letters 20220523 21

Herein, we report a new electrochemical method for alkoxy radical generation from alcohols using a proton-coupled electron transfer (PCET) approach, showcased via the deconstructive functionalization of cycloalkanols. The electrochemical method is applicable across a diverse array of substituted cycloalkanols, accessing a broad range of synthetically useful distally functionalized ketones. The orthogonal derivatization of the products has been demonstrated through chemoselective transformations, ...[more]

PMID: 35604008

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