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

Authors :
Allen BDW
Hareram MD
Seastram AC
McBride T
Wirth T
Browne DL
Morrill LC
Source :
Organic letters [Org Lett] 2019 Nov 15; Vol. 21 (22), pp. 9241-9246. Date of Electronic Publication: 2019 Nov 05.
Publication Year :
2019

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 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.

Details

Language :
English
ISSN :
1523-7052
Volume :
21
Issue :
22
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
31687826
Full Text :
https://doi.org/10.1021/acs.orglett.9b03652