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Allylic C-H Acetoxylation with a 4,5-Diazafluorenone-Ligated Palladium Catalyst: A Ligand-Based Strategy To Achieve Aerobic Catalytic Turnover

Alison N. Campbell, Paul B. White, Ilia A. Guzei and Shannon S. Stahl*

*Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States, Email: stahlchem.wisc.edu

A. N. Campbell, P. B. White, I. A. Guzei, S. S. Stahl, J. Am. Chem. Soc., 2010, 132, 15116-15119.

DOI: 10.1021/ja105829t (free Supporting Information)


Abstract

Use of 4,5-diazafluorenone as an ancillary ligand for Pd(OAc)2 enables terminal alkenes to be converted to linear allylic acetoxylation products in good yields and selectivity under O2. Mechanistic studies have revealed that the ligand facilitates C-O reductive elimination from a π-allyl-PdII intermediate, thereby eliminating the requirement for benzoquinone as stoichiometric oxidant in this key catalytic step.

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Key Words

Allylic Alcohols, Oxygen


ID: J48-Y2010-2970