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Communication

Palladium-Catalyzed Oxygenation of Unactivated sp³ C−H Bonds

Supporting Info

Lopa V. Desai, Kami L. Hull, and Melanie S. Sanford*

Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055

J. Am. Chem. Soc., 2004, 126 (31), pp 9542–9543

DOI: 10.1021/ja046831c

Publication Date (Web): July 16, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mssanfor@umich.edu

Abstract

This communication describes a new palladium-catalyzed method for the oxygenation of unactivated sp³ C−H bonds. A wide variety of alkane substrates containing readily available oxime and/or pyridine directing groups are oxidized with extremely high levels of chemo-, regio-, and in some cases diastereoselectivity. The substrate scope of these reactions is discussed, and the high selectivities are rationalized on the basis of the requirements of putative palladium alkyl intermediates.

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History

Published In Issue August 11, 2004
Received May 28, 2004

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Communication

Palladium-Catalyzed Oxygenation of Unactivated sp³ C−H Bonds