Mechanistic Study of Pd/NHC‐Catalyzed Sonogashira Reaction: Discovery of NHC‐Ethynyl Coupling Process
Тип публикации: Journal Article
Дата публикации: 2020-10-27
SCImago Q1
WOS Q2
БС1
SJR: 0.803
CiteScore: 5.8
Impact factor: 3.6
ISSN: 09476539, 15213765
PubMed ID:
32881095
General Chemistry
Catalysis
Organic Chemistry
Краткое описание
The product of a revealed transformation - NHC-ethynyl coupling - was observed as a catalyst transformation pathway in the Sonogashira cross-coupling, catalyzed by Pd/NHC complexes. The 2-ethynylated azolium salt was isolated in individual from and fully characterized, including the X-Ray analysis. A number of possible intermediates of this transformation with common formulae (NHC)xPd(C2Ph) (x = 1,2) were observed and subjected to collision-induced dissociation (CID) and infrared multiphoton dissociation (IRMPD) experiments studies to elucidate their structure. Measured bond dissociation energies (BDEs) and IRMPD spectra were in an excellent agreement with quantum calculations for coupling product π-complexes with Pd(0). Molecular dynamics simulations confirmed multiple observed CID fragmentation pathways. Performed study of catalyst evolution suggests the reported transformation to be considered in the development of new catalytic systems for alkyne functionalization reactions.
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Eremin D. B. et al. Mechanistic Study of Pd/NHC‐Catalyzed Sonogashira Reaction: Discovery of NHC‐Ethynyl Coupling Process // Chemistry - A European Journal. 2020. Vol. 26. No. 67. pp. 15672-15681.
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Eremin D. B., Boiko D. A., Kostyukovich A. Y., Burykina J. V., Denisova E. A., Anania M., Martens J., Berden G., Oomens J., Roithová J., Ananikov V. P. Mechanistic Study of Pd/NHC‐Catalyzed Sonogashira Reaction: Discovery of NHC‐Ethynyl Coupling Process // Chemistry - A European Journal. 2020. Vol. 26. No. 67. pp. 15672-15681.
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TY - JOUR
DO - 10.1002/chem.202003533
UR - https://doi.org/10.1002/chem.202003533
TI - Mechanistic Study of Pd/NHC‐Catalyzed Sonogashira Reaction: Discovery of NHC‐Ethynyl Coupling Process
T2 - Chemistry - A European Journal
AU - Eremin, Dmitry B.
AU - Boiko, Daniil A
AU - Kostyukovich, Alexander Yu.
AU - Burykina, Julia V
AU - Denisova, Ekaterina A
AU - Anania, Mariarosa
AU - Martens, Jonathan
AU - Berden, Giel
AU - Oomens, Jos
AU - Roithová, Jana
AU - Ananikov, Valentine P
PY - 2020
DA - 2020/10/27
PB - Wiley
SP - 15672-15681
IS - 67
VL - 26
PMID - 32881095
SN - 0947-6539
SN - 1521-3765
ER -
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@article{2020_Eremin,
author = {Dmitry B. Eremin and Daniil A Boiko and Alexander Yu. Kostyukovich and Julia V Burykina and Ekaterina A Denisova and Mariarosa Anania and Jonathan Martens and Giel Berden and Jos Oomens and Jana Roithová and Valentine P Ananikov},
title = {Mechanistic Study of Pd/NHC‐Catalyzed Sonogashira Reaction: Discovery of NHC‐Ethynyl Coupling Process},
journal = {Chemistry - A European Journal},
year = {2020},
volume = {26},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002/chem.202003533},
number = {67},
pages = {15672--15681},
doi = {10.1002/chem.202003533}
}
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MLA
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Eremin, Dmitry B., et al. “Mechanistic Study of Pd/NHC‐Catalyzed Sonogashira Reaction: Discovery of NHC‐Ethynyl Coupling Process.” Chemistry - A European Journal, vol. 26, no. 67, Oct. 2020, pp. 15672-15681. https://doi.org/10.1002/chem.202003533.
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