Issue 13, 2014
From the journal:

RSC Advances

Palladium-catalyzed oxidative C–O cross-coupling of ketene dithioacetals and carboxylic acids†

Deqiang Liang,ab   Mang Wang,*a   Ying Dong,a   Yaru Guoa  and  Qun Liu*a  

* Corresponding authors

a Department of Chemistry, Northeast Normal University, Changchun 130024, China
E-mail: wangm452@nenu.edu.cn, liuqun@nenu.edu.cn
Fax: +86-431-85099759
Tel: +86-431-85099759

b Department of Chemistry, Kunming University, Kunming 650214, China

Abstract

Direct oxidative C–O cross-coupling reaction between active alkenes and carboxylic acids is presented. By utilizing Pd(OAc)2 as a catalyst and PhI(OAc)2 as an oxidant, ketene dithioacetals were smoothly acyloxylated in carboxylic acid–water solution, affording a variety of vinyl esters in a highly selective way with high efficiency and good functional group tolerance. A plausible mechanism is proposed that features a vinyl iodonium species as key intermediate.

Graphical abstract: Palladium-catalyzed oxidative C–O cross-coupling of ketene dithioacetals and carboxylic acids

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Article information

DOI
https://doi.org/10.1039/C3RA47282E
Article type
Communication
Submitted
04 Dec 2013
Accepted
24 Dec 2013
First published
03 Jan 2014

RSC Adv., 2014,4, 6564-6567

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Palladium-catalyzed oxidative C–O cross-coupling of ketene dithioacetals and carboxylic acids

D. Liang, M. Wang, Y. Dong, Y. Guo and Q. Liu, RSC Adv., 2014, 4, 6564 DOI: 10.1039/C3RA47282E

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