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Palladium-catalyzed alkoxycarbonylation of terminal alkenes to produce α,β-unsaturated esters: the key role of acetonitrile as a ligand

journal contribution
posted on 08.08.2014 by Andrei Malkov, Nolwenn Derrien, Maciej Barlog, Pavel Kocovsky
A mild protocol has been developed for the Pd-catalyzed alkoxycarbonylation of terminal olefins to produce α,β-unsaturated esters with a wide range of substrates. Key features are the use of MeCN as solvent (and/or ligand) to control the reactivity of the intermediate Pd complexes and the combination of CO with O, which facilitates the Cu-mediated reoxidation of the Pd complex to Pd and prevents double carbonylation. Acetonitrile is the key! A mild protocol has been developed for the Pd-catalyzed alkoxycarbonylation of terminal olefins to produce α,β-unsaturated esters with a wide range of substrates (see scheme). Key features are the use of MeCN as a solvent (and/or ligand) to control the reactivity of the intermediate Pd complexes and the combination of CO with O, which facilitates the Cu-mediated reoxidation of Pd to Pd and prevents double carbonylation.

History

School

  • Science

Department

  • Chemistry

Published in

Chemistry - A European Journal

Volume

20

Issue

16

Pages

4542 - 4547

Citation

MALKOV, A.V. ... et al., 2014. Palladium-catalyzed alkoxycarbonylation of terminal alkenes to produce α,β-unsaturated esters: the key role of acetonitrile as a ligand. Chemistry: a European Journal, 20 (16), pp. 4542-4547.

Publisher

© Wiley-VCH

Version

AM (Accepted Manuscript)

Publication date

2014

Notes

This is the peer reviewed version of the following article: MALKOV, A.V. ... et al., 2014. Palladium-catalyzed alkoxycarbonylation of terminal alkenes to produce α,β-unsaturated esters: the key role of acetonitrile as a ligand. Chemistry: a European Journal, 20 (16), pp. 4542-4547, which has been published in final form at: http://dx.doi.org/10.1002/chem.201304798.

ISSN

0947-6539

eISSN

1521-3765

Language

en

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