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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 2014-08-08, 14:04 authored by Andrei MalkovAndrei Malkov, Nolwenn Derrien, Maciej Barlog, Pavel KocovskyA 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 JournalVolume
20Issue
16Pages
4542 - 4547Citation
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-VCHVersion
- AM (Accepted Manuscript)
Publication date
2014Notes
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
0947-6539eISSN
1521-3765Publisher version
Language
- en