Wacker-Type Oxidation of Internal Alkenes using Pd(Quinox) and TBHP

Ryan J. DeLuca, Jennifer L. Edwards, Laura D. Steffens, Brian W. Michel, Xiaoxiao Qiao, Chunyin Zhu, Silas P. Cook* and Matthew S. Sigman*

*Department of Chemistry, Indiana University, Bloomington, Indiana 47405, Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, United States, Email: sicookindiana.edu, sigmanchem.utah.edu

R. J. DeLuca, J. L. Edwards, L. D. Steffens, B. W. Michel, X. Qiao, C. Zhu, S. P. Cook, M. S. Sigman, J. Org. Chem., 2013, 78, 1682-1683.

DOI: 10.1021/jo302638v

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Abstract

The Pd-catalyzed TBHP-mediated Wacker-type oxidation of internal alkenes uses 2-(4,5-dihydro-2-oxazolyl)quinoline (Quinox) as ligand and TBHP as oxidant to deliver single ketone constitutional isomer products in a predictable fashion from electronically biased olefins.

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A General and Efficient Catalyst System for a Wacker-Type Oxidation Using TBHP as the Terminal Oxidant: Application to Classically Challenging Substrates

B. W. Michel, A. M. Camelio, C. N. Cornell, M. S. Sigman, J. Am. Chem. Soc., 2009, 131, 6076-6077.

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Key Words

Wacker Oxidation, TBHP

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ID: J42-Y2013-0480