Lewis Acid Induced β-Elimination from a Nickelalactone: Efforts toward Acrylate Production from CO2and Ethylene
Publication type: Journal Article
Publication date: 2013-03-21
scimago Q2
wos Q1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
The Lewis acid tris(pentafluorophenyl)borane was found to rapidly promote ring-opening β-hydride elimination in a 1,1′-bis(diphenylphosphino)ferrocene (dppf) nickelalactone complex under ambient conditions. The thermodynamic product of nickelalactone ring-opening was characterized as (dppf)Ni(CH(CH3)CO2BArf3), the result of β-hydride elimination and subsequent 2,1-insertion from a transient nickel(II) acrylate hydride intermediate. Treatment of (dppf)Ni(CH(CH3)CO2BArf3) with a nitrogen-containing base afforded a diphosphine nickel(0) η2-acryl borate adduct. Formation of the diphosphine nickel(0) η2-acryl borate adduct completes a net conversion of nickelalactone to acrylate species, a significant obstacle to catalytic acrylate production from CO2 and ethylene. Displacement of the η2-acrylate fragment from the nickel center was accomplished by addition of ethylene to yield a free acrylate salt and (dppf)Ni(CH2═CH2).
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67
Total citations:
67
Citations from 2024:
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(10.45%)
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GOST
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Dong J. et al. Lewis Acid Induced β-Elimination from a Nickelalactone: Efforts toward Acrylate Production from CO2and Ethylene // Organometallics. 2013. Vol. 32. No. 7. pp. 2152-2159.
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Dong J., Schmeier T. J., Williard P., Hazari N., Bernskoetter W. H. Lewis Acid Induced β-Elimination from a Nickelalactone: Efforts toward Acrylate Production from CO2and Ethylene // Organometallics. 2013. Vol. 32. No. 7. pp. 2152-2159.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/om400025h
UR - https://doi.org/10.1021/om400025h
TI - Lewis Acid Induced β-Elimination from a Nickelalactone: Efforts toward Acrylate Production from CO2and Ethylene
T2 - Organometallics
AU - Dong, Jin
AU - Schmeier, Timothy J
AU - Williard, P.
AU - Hazari, Nilay
AU - Bernskoetter, Wesley H
PY - 2013
DA - 2013/03/21
PB - American Chemical Society (ACS)
SP - 2152-2159
IS - 7
VL - 32
SN - 0276-7333
SN - 1520-6041
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2013_Dong,
author = {Jin Dong and Timothy J Schmeier and P. Williard and Nilay Hazari and Wesley H Bernskoetter},
title = {Lewis Acid Induced β-Elimination from a Nickelalactone: Efforts toward Acrylate Production from CO2and Ethylene},
journal = {Organometallics},
year = {2013},
volume = {32},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/om400025h},
number = {7},
pages = {2152--2159},
doi = {10.1021/om400025h}
}
Cite this
MLA
Copy
Dong, Jin, et al. “Lewis Acid Induced β-Elimination from a Nickelalactone: Efforts toward Acrylate Production from CO2and Ethylene.” Organometallics, vol. 32, no. 7, Mar. 2013, pp. 2152-2159. https://doi.org/10.1021/om400025h.