Issue 11, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
26 Jun 2013
Accepted
12 Jul 2013
First published
15 Jul 2013

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

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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