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Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals.

ABSTRACT: A manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols has been developed. This electrochemical method provides access to alkoxy radicals from alcohols and exhibits a broad substrate scope, with various cyclopropanols and cyclobutanols converted into synthetically useful ?- and ?-chlorinated ketones (40 examples). Furthermore, the combination of recirculating flow electrochemistry and continuous inline purification was employed to access products on a gram scale.

SUBMITTER: Allen BDW

PROVIDER: S-EPMC7007279 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals.

Allen Benjamin D W BDW Hareram Mishra Deepak MD Seastram Alex C AC McBride Tom T Wirth Thomas T Browne Duncan L DL Morrill Louis C LC

Organic letters 20191105 22

A manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols has been developed. This electrochemical method provides access to alkoxy radicals from alcohols and exhibits a broad substrate scope, with various cyclopropanols and cyclobutanols converted into synthetically useful β- and γ-chlorinated ketones (40 examples). Furthermore, the combination of recirculating flow electrochemistry and continuous inline purification was employed to access products on a gram scale. ...[more]

PMID: 31687826

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