Issue 11, 2013
From the journal:

New Journal of Chemistry

Liberation of methyl acrylate from metallalactone complexes via M–O ring opening (M = Ni, Pd) with methylation agents†

S. Y. Tina Lee,ab   Amylia Abdul Ghani,ab   Valerio D'Elia,*b   Mirza Cokoja,a   Wolfgang A. Herrmann,*a   Jean-Marie Basset*b  and  Fritz E. Kühn*a  

* Corresponding authors

a Chair of Inorganic Chemistry/Molecular Catalysis, Catalysis Research Center, Technische Universität München, Ernst-Otto-Fischer-Straße 1, D-85747 Garching bei München, Germany
E-mail: wolfgangherrmann@ch.tum.de, fritz.kuehn@ch.tum.de
Fax: +49 89 289 13473
Tel: +49 89 289 13080

b KAUST Catalysis Center, King Abdullah University of Science and Technology, 23955 Thuwal, Kingdom of Saudi Arabia
E-mail: valerio.delia@kaust.edu.sa, jeanmarie.basset@kaust.edu.sa

Abstract

Ring opening of various nickela- and palladalactones induced by the cleavage of the M–O bond by methyl trifluoromethanesulfonate (MeOTf) and methyl iodide (MeI) is examined. Experimental evidence supports the mechanism of ring opening by the alkylating agent followed by β-H elimination leading to methyl acrylate and a metal-hydride species. MeOTf shows by far higher efficiency in the lactone ring opening than any other methylating agent including the previously reported methyl iodide.

Graphical abstract: Liberation of methyl acrylate from metallalactone complexes via M–O ring opening (M = Ni, Pd) with methylation agents

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Article information

DOI
https://doi.org/10.1039/C3NJ00693J
Article type
Paper
Submitted
26 Jun 2013
Accepted
12 Jul 2013
First published
15 Jul 2013

New J. Chem., 2013,37, 3512-3517

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Liberation of methyl acrylate from metallalactone complexes via M–O ring opening (M = Ni, Pd) with methylation agents

S. Y. T. Lee, A. A. Ghani, V. D'Elia, M. Cokoja, W. A. Herrmann, J. Basset and F. E. Kühn, New J. Chem., 2013, 37, 3512 DOI: 10.1039/C3NJ00693J

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