Organic Chemistry Portal

Abstracts

Search:

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: rhgcaltech.edu

P. Teo, Z. K. Wickens, G. Dong, R. H. Grubbs, Org. Lett., 2012, 14, 3237-3239.

DOI: 10.1021/ol301240g (free Supporting Information)


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