Issue 13, 2015

Olefins from biomass feedstocks: catalytic ester decarbonylation and tandem Heck-type coupling

Abstract

With the goal of avoiding the need for anhydride additives, the catalytic decarbonylation of p-nitrophenylesters of aliphatic carboxylic acids to their corresponding olefins, including commodity monomers like styrene and acrylates, has been developed. The reaction is catalyzed by palladium complexes in the absence of added ligands and is promoted by alkali/alkaline-earth metal halides. Combination of catalytic decarbonylation and Heck-type coupling with aryl esters in a single pot process demonstrates the viability of employing a carboxylic acid as a “masked olefin” in synthetic processes.

Graphical abstract: Olefins from biomass feedstocks: catalytic ester decarbonylation and tandem Heck-type coupling

Supplementary files

Article information

Article type
Communication
Submitted
11 Nov 2014
Accepted
03 Jan 2015
First published
12 Jan 2015

Chem. Commun., 2015,51, 2731-2733

Olefins from biomass feedstocks: catalytic ester decarbonylation and tandem Heck-type coupling

A. John, L. T. Hogan, M. A. Hillmyer and W. B. Tolman, Chem. Commun., 2015, 51, 2731 DOI: 10.1039/C4CC09003A

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