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J Org Chem. 2016 Oct 7;81(19):8673-8695. Epub 2016 Sep 26.

Synthesis of Ketones and Esters from Heteroatom-Functionalized Alkenes by Cobalt-Mediated Hydrogen Atom Transfer.

Author information

1
Department of Chemistry, Yale University , New Haven, Connecticut 06520, United States.
2
Department of Pharmacology, Yale School of Medicine , New Haven, Connecticut 06520, United States.

Abstract

Cobalt bis(acetylacetonate) is shown to mediate hydrogen atom transfer to a broad range of functionalized alkenes; in situ oxidation of the resulting alkylradical intermediates, followed by hydrolysis, provides expedient access to ketones and esters. By modification of the alcohol solvent, different alkyl ester products may be obtained. The method is compatible with a number of functional groups including alkenyl halides, sulfides, triflates, and phosphonates and provides a mild and practical alternative to the Tamao-Fleming oxidation of vinylsilanes and the Arndt-Eistert homologation.

PMID:
27598718
DOI:
10.1021/acs.joc.6b01709

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