Efficient and Highly Aldehyde Selective Wacker Oxidation
Peili Teo, Zachary K. Wickens, Guangbin Dong and Robert H. Grubbs*
*Arnold and Mabel Beckman Laboratory of Chemical Synthesis,
Division of Chemistry and Chemical Engineering, California Institute of
Technology, Pasadena, California 91125, Email: rhg
caltech.edu
P. Teo, Z. K. Wickens, G. Dong, R. H. Grubbs, Org. Lett., 2012, 14, 3237-3239.
DOI: 10.1021/ol301240g
Abstract
In the presence of PdCl2(MeCN)2, 1,4-benzoquinone, and t-BuOH, aryl-substituted olefins can selectively be oxidized to aldehydes. In this efficient and aldehyde-selective Wacker oxidation, very good yield of aldehyde can be obtained, and up to 99% selectivity can be achieved with styrene-related substrates.
see article for more examples
proposed reaction pathway
Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes
Z. K. Wickens, K. Skakuj, B. Morandi, R. H. Grubbs, J. Am. Chem. Soc., 2014, 136, 890-893.
Key Words
Wacker-Tsuji Oxidation, 1,4-Benzoquinone, Aldehydes
ID: J54-Y2012-2080
