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Palladium-Catalyzed Aerobic Acetoxylation of Benzene using NOx-Based Redox Mediators.

Authors
  • Zultanski, Susan L1
  • Stahl, Shannon S1
  • 1 Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave., Madison, Wisconsin 53706, United States. , (United States)
Type
Published Article
Journal
Journal of Organometallic Chemistry
Publisher
Elsevier
Publication Date
May 01, 2015
Volume
52
Pages
97–102
Identifiers
PMID: 25843978
Source
Medline
Keywords
License
Unknown

Abstract

Palladium-catalyzed methods for C-H oxygenation with O2 as the stoichiometric oxidant are limited. Here, we describe the use of nitrite and nitrate sources as NOx-based redox mediators in the acetoxylation of benzene. The conditions completely avoid formation of biphenyl as a side product, and strongly favor formation of phenyl acetate over nitrobenzene (PhOAc:PhNO2 ratios up to 40:1). Under the optimized reaction conditions, with 0.1 mol% Pd(OAc)2, 136 turnovers of Pd are achieved with only 1 atm of O2 pressure.

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