Organometallics, volume 42, issue 3, pages 218-234
Properties and Catalytic Activity of Hoveyda–Grubbs-Type Catalysts with an S → Ru Coordination Bond in a Six-Membered Chelate Ring
Kumandin Pavel A.
1
,
Novikov Roman G.
2
,
Vinokurova Marina A.
1
,
Novikov Anton P.
3
,
Polianskaia Daria K
1
,
Polyanskii Kirill B.
1
,
Publication type: Journal Article
Publication date: 2023-01-27
Journal:
Organometallics
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor: 2.8
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
This work continues our group’s research into the synthesis and study of the catalytic activity of ruthenium chelates with various heteroatoms (O, S, N, and Se) in a six-membered ring. It was found that second-generation Hoveyda–Grubbs-type catalysts containing a sulfur-ruthenium coordinate bond in a six-membered chelate ring can be prepared easily and in high yields using standard procedures, based on the interaction between (2-vinylbenzyl)sulfanes and Ind II (the common precursor for Ru-complex synthesis). The obtained ruthenium derivatives, with a donor-acceptor S → Ru bond, can exist in two isomeric forms according to the arrangement of substituents around the central metal atom. Kinetically controlled trans-isomers are formed at temperatures below 80 °C in heptane and are less thermodynamically stable compared with cis-isomers, which arise under heating of trans-S-chelates in 1,2-dichloroethane at 110 °C. The structures of all the cis- and trans-isomers were determined and characterized in detail by X-ray diffraction and nuclear magnetic resonance. The study of the activity of the catalysts in standard ring-closing metathesis and ring-opening metathesis polymerization reactions showed that the cis-isomers are inactive in the absence of thermal or UV activation, while trans-complexes of the same type display excellent catalytic properties at r.t. that are superior to those of the commercially available HG-II catalyst. The structure, spectral characteristics, and catalytic activity of the catalysts containing an S → Ru bond in a six-membered chelate ring were compared with their five-membered analogues obtained in previous works.
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1 publication, 33.33%
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Kumandin P. A. et al. Properties and Catalytic Activity of Hoveyda–Grubbs-Type Catalysts with an S → Ru Coordination Bond in a Six-Membered Chelate Ring // Organometallics. 2023. Vol. 42. No. 3. pp. 218-234.
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Kumandin P. A., Antonova A. S., Novikov R. G., Vasilyev K. A., Vinokurova M. A., Grigoriev M. S., Novikov A. P., Polianskaia D. K., Polyanskii K. B., Zubkov F. I. Properties and Catalytic Activity of Hoveyda–Grubbs-Type Catalysts with an S → Ru Coordination Bond in a Six-Membered Chelate Ring // Organometallics. 2023. Vol. 42. No. 3. pp. 218-234.
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TY - JOUR
DO - 10.1021/acs.organomet.2c00556
UR - https://doi.org/10.1021%2Facs.organomet.2c00556
TI - Properties and Catalytic Activity of Hoveyda–Grubbs-Type Catalysts with an S → Ru Coordination Bond in a Six-Membered Chelate Ring
T2 - Organometallics
AU - Kumandin, Pavel A.
AU - Antonova, Alexandra S
AU - Novikov, Roman G.
AU - Vasilyev, Kirill A.
AU - Vinokurova, Marina A.
AU - Grigoriev, Mikhail S.
AU - Novikov, Anton P.
AU - Polianskaia, Daria K
AU - Polyanskii, Kirill B.
AU - Zubkov, Fedor I.
PY - 2023
DA - 2023/01/27 00:00:00
PB - American Chemical Society (ACS)
SP - 218-234
IS - 3
VL - 42
SN - 0276-7333
SN - 1520-6041
ER -
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@article{2023_Kumandin,
author = {Pavel A. Kumandin and Alexandra S Antonova and Roman G. Novikov and Kirill A. Vasilyev and Marina A. Vinokurova and Mikhail S. Grigoriev and Anton P. Novikov and Daria K Polianskaia and Kirill B. Polyanskii and Fedor I. Zubkov},
title = {Properties and Catalytic Activity of Hoveyda–Grubbs-Type Catalysts with an S → Ru Coordination Bond in a Six-Membered Chelate Ring},
journal = {Organometallics},
year = {2023},
volume = {42},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021%2Facs.organomet.2c00556},
number = {3},
pages = {218--234},
doi = {10.1021/acs.organomet.2c00556}
}
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Kumandin, Pavel A., et al. “Properties and Catalytic Activity of Hoveyda–Grubbs-Type Catalysts with an S → Ru Coordination Bond in a Six-Membered Chelate Ring.” Organometallics, vol. 42, no. 3, Jan. 2023, pp. 218-234. https://doi.org/10.1021%2Facs.organomet.2c00556.