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Synthesis 2011(16): 2579-2589  
DOI: 10.1055/s-0030-1260087
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Ligand-Directed Oxidative Functionalization of Cyclopropanes

Asako Kubota, Melanie S. Sanford*
University of Michigan, Department of Chemistry, 930 N. University Ave, Ann Arbor, MI 48109, USA
Fax: +1(734)6474865; e-Mail: mssanfor@umich.edu;
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Publication History

Received 15 March 2011
Publication Date:
08 July 2011 (online)

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Abstract

This report describes the palladium-catalyzed functionalization of cyclopropanes containing oxazoline, oxime ether, and pyridine directing groups. Three different oxidants were examined in these studies: IOAc, PhI(OAc)2, and benzoquinone. The reactions yielded products derived from 2˚ sp³ C-H functionalization and/or C-C activation of the cyclopropane ring. The outcome and the product distributions were highly dependent on the structure of the substrate and the nature of the oxidant.

Key words

cyclopropane - C-H functionalization - palladium - cleavage - homogeneous catalysis

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