Journal of Organic Chemistry, volume 87, issue 15, pages 10199-10207
Sulfonium and Selenonium Salts as Noncovalent Organocatalysts for the Multicomponent Groebke–Blackburn–Bienaymé Reaction
Publication type: Journal Article
Publication date: 2022-07-20
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Sulfonium and selenonium salts, represented by S-aryl dibenzothiophenium and Se-aryl dibenzoselenophenium triflates, were found to exhibit remarkable catalytic activity in the model Groebke-Blackburn-Bienaymé reaction. Kinetic analysis and density functional theory (DFT) calculations indicated that their catalytic effect is induced by the ligation of the reaction substrates to the σ-holes on the S or Se atom of the cations. The experimental data indicated that although 10-fold excess of the chloride totally inhibits the catalytic activity of the sulfonium salts, the selenonium salt remains catalytically active, which can be explained by the experimentally found lower binding constant of the selenonium derivative to chloride in comparison with the sulfonium analogue. Both types of salts exhibit lower catalytic activity in the model reaction than dibenziodolium species.
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Ilin M. V. et al. Sulfonium and Selenonium Salts as Noncovalent Organocatalysts for the Multicomponent Groebke–Blackburn–Bienaymé Reaction // Journal of Organic Chemistry. 2022. Vol. 87. No. 15. pp. 10199-10207.
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Ilin M. V., Novikov A. S., Venter G. J. S. Sulfonium and Selenonium Salts as Noncovalent Organocatalysts for the Multicomponent Groebke–Blackburn–Bienaymé Reaction // Journal of Organic Chemistry. 2022. Vol. 87. No. 15. pp. 10199-10207.
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TY - JOUR
DO - 10.1021/acs.joc.2c01141
UR - https://doi.org/10.1021%2Facs.joc.2c01141
TI - Sulfonium and Selenonium Salts as Noncovalent Organocatalysts for the Multicomponent Groebke–Blackburn–Bienaymé Reaction
T2 - Journal of Organic Chemistry
AU - Ilin, Mikhail V
AU - Novikov, Alexander S.
AU - Venter, Gertruida J. S.
PY - 2022
DA - 2022/07/20 00:00:00
PB - American Chemical Society (ACS)
SP - 10199-10207
IS - 15
VL - 87
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2022_Ilin,
author = {Mikhail V Ilin and Alexander S. Novikov and Gertruida J. S. Venter},
title = {Sulfonium and Selenonium Salts as Noncovalent Organocatalysts for the Multicomponent Groebke–Blackburn–Bienaymé Reaction},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021%2Facs.joc.2c01141},
number = {15},
pages = {10199--10207},
doi = {10.1021/acs.joc.2c01141}
}
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Ilin, Mikhail V., et al. “Sulfonium and Selenonium Salts as Noncovalent Organocatalysts for the Multicomponent Groebke–Blackburn–Bienaymé Reaction.” Journal of Organic Chemistry, vol. 87, no. 15, Jul. 2022, pp. 10199-10207. https://doi.org/10.1021%2Facs.joc.2c01141.