Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals

Benjamin D. W. Allen, Mishra Deepak Hareram, Alex C. Seastram, Tom McBride, Thomas Wirth, Duncan L. Browne, Louis C. Morrill

Organic Letters · 2019 · 102 citations · 57 references

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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.

References

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