Advanced Synthesis and Catalysis, volume 363, issue 19, pages 4590-4604
Activated Hoveyda‐Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde
2
Polpharma SA Pharmaceutical Works Pelplińska 19 83-200 Starogard Gdański Poland
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Publication type: Journal Article
Publication date: 2021-08-11
Journal:
Advanced Synthesis and Catalysis
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.4
ISSN: 16154150, 16154169
General Chemistry
Abstract
Two EWG-activated Hoveyda-Grubbs-type ruthenium complexes (Sil-II and Sil-II’) were obtained, characterized, and screened in a set of olefin metathesis reactions. These catalysts were conveniently synthesized from a commercially available pharmaceutical building block – Sildenafil aldehyde – in two steps only. Stability and catalytic activity tests disclosed that the bulkier NHC-ligand bearing catalyst Sil-II’ is visibly more stable and productive than its smaller NHC-analogue Sil-II. Good application profile of catalyst Sil-II’ was confirmed in a set of diverse metathesis reactions including ring-closing metathesis (RCM) and cross-metathesis (CM) of complex polyfunctional substrates of medicinal chemistry interest, including a challenging macrocyclization of the Pacritinib precursor. Compatibility of the new catalyst with various green solvents was checked and metathesis of Sildenafil and Tadalafil-based substrates was successfully conducted in acetone. The mechanism of Sil-II’ initiation has been investigated through kinetic experiments unveiling that the decrease of the steric hindrance of the chelating alkoxy moiety (from iPrO to EtO) favors the interchange initiation pathway over the typical dissociation pathway for other popular 2nd generation Hoveyda-Grubbs catalysts.
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- We do not take into account publications without a DOI.
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Monsigny L. et al. Activated Hoveyda‐Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde // Advanced Synthesis and Catalysis. 2021. Vol. 363. No. 19. pp. 4590-4604.
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Monsigny L., Piątkowski J., Trzybinski D., Woźniak K., Nienałtowski T., Kajetanowicz A., Grela K. Activated Hoveyda‐Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde // Advanced Synthesis and Catalysis. 2021. Vol. 363. No. 19. pp. 4590-4604.
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TY - JOUR
DO - 10.1002/adsc.202100669
UR - https://doi.org/10.1002/adsc.202100669
TI - Activated Hoveyda‐Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde
T2 - Advanced Synthesis and Catalysis
AU - Nienałtowski, Tomasz
AU - Monsigny, Louis
AU - Piątkowski, Jakub
AU - Trzybinski, Damian
AU - Woźniak, Krzysztof
AU - Kajetanowicz, Anna
AU - Grela, Karol
PY - 2021
DA - 2021/08/11 00:00:00
PB - Wiley
SP - 4590-4604
IS - 19
VL - 363
SN - 1615-4150
SN - 1615-4169
ER -
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@article{2021_Monsigny,
author = {Tomasz Nienałtowski and Louis Monsigny and Jakub Piątkowski and Damian Trzybinski and Krzysztof Woźniak and Anna Kajetanowicz and Karol Grela},
title = {Activated Hoveyda‐Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde},
journal = {Advanced Synthesis and Catalysis},
year = {2021},
volume = {363},
publisher = {Wiley},
month = {aug},
url = {https://doi.org/10.1002/adsc.202100669},
number = {19},
pages = {4590--4604},
doi = {10.1002/adsc.202100669}
}
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Monsigny, Louis, et al. “Activated Hoveyda‐Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde.” Advanced Synthesis and Catalysis, vol. 363, no. 19, Aug. 2021, pp. 4590-4604. https://doi.org/10.1002/adsc.202100669.