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

Xiaoshen Ma and Seth B. Herzon*

*Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States, Email: seth.herzonyale.edu

X. Ma, S. B. Herzon, J. Org. Chem., 2016, 81, 8673-8695.

DOI: 10.1021/acs.joc.6b01709 (free Supporting Information)


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Abstract

Cobalt bis(acetylacetonate) mediates 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. This method is compatible with a number of functional groups and provides a mild and practical alternative to the Tamao-Fleming oxidation of vinylsilanes and the Arndt-Eistert homologation.

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Key Words

α-hydroxy ketones, esters


ID: J42-Y2016