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Metal-Free, Aerobic Dioxygenation of Alkenes Using Simple Hydroxamic Acid Derivatives

Benjamin C. Giglio, Valerie A. Schmidt and Erik J. Alexanian*

*Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States, Email: ejaemail.unc.edu

B. C. Giglio, V. A. Schmidt, E. J. Alexanian, J. Am. Chem. Soc., 2011, 133, 13320-13322.

DOI: 10.1021/ja206306f (free Supporting Information)


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Abstract

A dioxygenation of alkenes using molecular oxygen and a simple, readily prepared hydroxamic acid derivative in the presence of a radical initiator offers an alternative to common dioxygenation processes catalyzed by precious transition metals. This transformation capitalizes on the unique reactivity profile of hydroxamic acid derivatives in radical-mediated alkene addition processes.

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Key Words

dihydroxylation, oxygen


ID: J48-Y2011-2350