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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

Brian W. Michel, Andrew M. Camelio, Candace N. Cornell and Matthew S. Sigman*

*Department of Chemistry, University of Utah, 315 S 1400 E, Salt Lake City, Utah 84112-085, Email: sigmanchem.utah.edu

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

DOI: 10.1021/ja901212h (free Supporting Information)


Abstract

Utilizing the rapidly synthesized Quinox ligand and commercially available aqueous TBHP, a Wacker-type oxidation efficiently converts even traditionally challenging substrates such as protected allylic alcohols to the corresponding oxidized products. Enantioenriched substrates undergo oxidation with complete retention of enantiomeric excess.

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

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.


Key Words

Wacker-Tsuji Oxidation, TBHP


ID: J48-Y2009-1430