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

S. Y Tina Lee; Amylia Abdul Ghani; Valerio D’Elia; Mirza Cokoja; Wolfgang A. Herrmann; Jean-Marie Basset; Fritz Kühn

doi:10.1039/c3nj00693j

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

S. Y Tina Lee, Amylia Abdul Ghani, Valerio D’Elia, Mirza Cokoja, Wolfgang A. Herrmann, Jean-Marie Basset, Fritz Kühn

Research output: Contribution to journal › Article › peer-review

42 Scopus citations

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. © 2013 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Original language	English (US)
Pages (from-to)	3512
Journal	New Journal of Chemistry
Volume	37
Issue number	11
DOIs	https://doi.org/10.1039/c3nj00693j
State	Published - 2013

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01

ASJC Scopus subject areas

Materials Chemistry
General Chemistry
Catalysis

Access to Document

10.1039/c3nj00693j

Cite this

@article{84388da6806146259a3386711f30ab1a,

title = "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. {\textcopyright} 2013 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.",

author = "Lee, {S. Y Tina} and Ghani, {Amylia Abdul} and Valerio D{\textquoteright}Elia and Mirza Cokoja and Herrmann, {Wolfgang A.} and Jean-Marie Basset and Fritz K{\"u}hn",

note = "KAUST Repository Item: Exported on 2020-10-01",

year = "2013",

doi = "10.1039/c3nj00693j",

language = "English (US)",

volume = "37",

pages = "3512",

journal = "New Journal of Chemistry",

issn = "1144-0546",

publisher = "Royal Society of Chemistry",

number = "11",

}

TY - JOUR

T1 - Liberation of methyl acrylate from metallalactone complexes via M-O ring opening (M = Ni, Pd) with methylation agents

AU - Lee, S. Y Tina

AU - Ghani, Amylia Abdul

AU - D’Elia, Valerio

AU - Cokoja, Mirza

AU - Herrmann, Wolfgang A.

AU - Basset, Jean-Marie

AU - Kühn, Fritz

N1 - KAUST Repository Item: Exported on 2020-10-01

PY - 2013

Y1 - 2013

N2 - 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. © 2013 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

AB - 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. © 2013 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

UR - http://hdl.handle.net/10754/562536

UR - http://xlink.rsc.org/?DOI=c3nj00693j

UR - http://www.scopus.com/inward/record.url?scp=84885813748&partnerID=8YFLogxK

U2 - 10.1039/c3nj00693j

DO - 10.1039/c3nj00693j

M3 - Article

SN - 1144-0546

VL - 37

SP - 3512

JO - New Journal of Chemistry

JF - New Journal of Chemistry

IS - 11

ER -

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

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this