Advanced Synthesis and Catalysis
Fast Olefin Metathesis: Synthesis of 2-Aryloxy-Substituted Hoveyda-Type Complexes and Application in Ring-Closing Metathesis
Publication type: Journal Article
Publication date: 2013-01-16
Journal:
Advanced Synthesis and Catalysis
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.4
ISSN: 16154150, 16154169
General Chemistry
Abstract
Four 1-(4-R-phenoxy)-2-ethenylbenzenes (R=NMe2, H, Cl, NO2) 4a, 4b, 4c and 4d were reacted with the ruthenium complexes [RuCl2(NHC)(3-phenylindenylidene)(py)] in the presence of a protic resin to result in the formation of the respective Hoveyda-type complexes 5a–d {NHC=SIMes [1,3-bis(2,4,6-trimethylphenylimidazolin)-2-ylidene]} and 6a–d {NHC=SIPr [1,3-bis(2,6-diisopropylphenylimidazolin)-2-ylidene]} in 66–84% yield. The lower steric bulk and the decreased donation of the diaryl ether oxygen atoms in complexes 5 and 6 led to rapidly initiating precatalysts. The Ru(II/III) redox potentials of complexes 6 were determined (6a–d: ΔE=0.89–1.08 V). In the crystal structure of 5b two independent molecules were observed in the unit cell, displaying RuO distances of 226.6(4) and 230.5(3) pm. The catalytic performance of complexes 5 and 6 in various ring-closing metathesis (RCM) reactions was studied. Catalyst loadings of between 15–200 ppm are sufficient for the formation of >90% yield of the respective cyclic products. Complex 6b catalyzes the formation of N-protected 2,5-dihydropyrroles with up to TON 64,000 and TOF 256,000 h−1, of the N-protected 1,2,3,6- tetrahydropyridines with up to TON 18,200 and TOF 73,000 h−1 and of the N-protected 2,3,6,7-tetrahydroazepines with up to TON 8,100 and TOF 32,000 h−1 with yields ranging between 77 and 96%.
Top-30
Citations by journals
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European Journal of Inorganic Chemistry
2 publications, 14.29%
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ACS Catalysis
2 publications, 14.29%
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Beilstein Journal of Organic Chemistry
1 publication, 7.14%
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1 publication, 7.14%
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ChemPhysChem
1 publication, 7.14%
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1 publication, 7.14%
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1 publication, 7.14%
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Macromolecules
1 publication, 7.14%
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Chemical Reviews
1 publication, 7.14%
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Russian Chemical Reviews
1 publication, 7.14%
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Citations by publishers
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3
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5
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7
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Wiley
7 publications, 50%
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American Chemical Society (ACS)
4 publications, 28.57%
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Beilstein-Institut
1 publication, 7.14%
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Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 7.14%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 7.14%
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- We do not take into account publications 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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Kos P., Savka R., Plenio H. Fast Olefin Metathesis: Synthesis of 2-Aryloxy-Substituted Hoveyda-Type Complexes and Application in Ring-Closing Metathesis // Advanced Synthesis and Catalysis. 2013.
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Kos P., Savka R., Plenio H. Fast Olefin Metathesis: Synthesis of 2-Aryloxy-Substituted Hoveyda-Type Complexes and Application in Ring-Closing Metathesis // Advanced Synthesis and Catalysis. 2013.
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TY - JOUR
DO - 10.1002/adsc.201200956
UR - https://doi.org/10.1002/adsc.201200956
TI - Fast Olefin Metathesis: Synthesis of 2-Aryloxy-Substituted Hoveyda-Type Complexes and Application in Ring-Closing Metathesis
T2 - Advanced Synthesis and Catalysis
AU - Kos, Pavlo
AU - Savka, Roman
AU - Plenio, H.
PY - 2013
DA - 2013/01/16 00:00:00
PB - Wiley
SN - 1615-4150
SN - 1615-4169
ER -
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@article{2013_Kos,
author = {Pavlo Kos and Roman Savka and H. Plenio},
title = {Fast Olefin Metathesis: Synthesis of 2-Aryloxy-Substituted Hoveyda-Type Complexes and Application in Ring-Closing Metathesis},
journal = {Advanced Synthesis and Catalysis},
year = {2013},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1002/adsc.201200956},
doi = {10.1002/adsc.201200956}
}