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Carbohydrate‐Functionalized Triazolylidene Iridium Complexes: Hydrogenation Catalysis in Water with Asymmetric Induction

Two sets of carbohydrate‐NHC hybrid iridium complexes were synthesised in order to combine properties of carbohydrates and triazolylidene (trz) ligands in organometallic catalysis. One set features a direct trz linkage to the anomeric carbohydrate carbon, while the second set is comprised of an ethy...

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Autores principales: Byrne, Joseph P., Delgado, Lidia, Paradisi, Francesca, Albrecht, Martin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9310948/
https://www.ncbi.nlm.nih.gov/pubmed/35910522
http://dx.doi.org/10.1002/cctc.202200086
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author Byrne, Joseph P.
Delgado, Lidia
Paradisi, Francesca
Albrecht, Martin
author_facet Byrne, Joseph P.
Delgado, Lidia
Paradisi, Francesca
Albrecht, Martin
author_sort Byrne, Joseph P.
collection PubMed
description Two sets of carbohydrate‐NHC hybrid iridium complexes were synthesised in order to combine properties of carbohydrates and triazolylidene (trz) ligands in organometallic catalysis. One set features a direct trz linkage to the anomeric carbohydrate carbon, while the second set is comprised of an ethyl linker between the two functional units. Deprotection of the carbohydrate afforded hybrid complexes that efficiently catalyse the direct hydrogenation of ketones in water. The catalytic activity of the hybrid complexes was influenced by the pH of the aqueous medium and surpassed the activity of carbohydrate‐free or acetyl‐protected analogues (>90 % vs 13 % yield). While no enantiomeric induction was observed for the ethyl‐linked hybrids, a moderate enantiomeric excess (ee) was induced by the directly linked systems. Moreover, these carbohydrate‐trz hybrid complexes displayed mixed inhibitory activity towards a glycosidase from H. orenii that contain a glucose binding site.
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spelling pubmed-93109482022-07-29 Carbohydrate‐Functionalized Triazolylidene Iridium Complexes: Hydrogenation Catalysis in Water with Asymmetric Induction Byrne, Joseph P. Delgado, Lidia Paradisi, Francesca Albrecht, Martin ChemCatChem Research Articles Two sets of carbohydrate‐NHC hybrid iridium complexes were synthesised in order to combine properties of carbohydrates and triazolylidene (trz) ligands in organometallic catalysis. One set features a direct trz linkage to the anomeric carbohydrate carbon, while the second set is comprised of an ethyl linker between the two functional units. Deprotection of the carbohydrate afforded hybrid complexes that efficiently catalyse the direct hydrogenation of ketones in water. The catalytic activity of the hybrid complexes was influenced by the pH of the aqueous medium and surpassed the activity of carbohydrate‐free or acetyl‐protected analogues (>90 % vs 13 % yield). While no enantiomeric induction was observed for the ethyl‐linked hybrids, a moderate enantiomeric excess (ee) was induced by the directly linked systems. Moreover, these carbohydrate‐trz hybrid complexes displayed mixed inhibitory activity towards a glycosidase from H. orenii that contain a glucose binding site. John Wiley and Sons Inc. 2022-03-11 2022-04-07 /pmc/articles/PMC9310948/ /pubmed/35910522 http://dx.doi.org/10.1002/cctc.202200086 Text en © 2022 The Authors. ChemCatChem published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Research Articles
Byrne, Joseph P.
Delgado, Lidia
Paradisi, Francesca
Albrecht, Martin
Carbohydrate‐Functionalized Triazolylidene Iridium Complexes: Hydrogenation Catalysis in Water with Asymmetric Induction
title Carbohydrate‐Functionalized Triazolylidene Iridium Complexes: Hydrogenation Catalysis in Water with Asymmetric Induction
title_full Carbohydrate‐Functionalized Triazolylidene Iridium Complexes: Hydrogenation Catalysis in Water with Asymmetric Induction
title_fullStr Carbohydrate‐Functionalized Triazolylidene Iridium Complexes: Hydrogenation Catalysis in Water with Asymmetric Induction
title_full_unstemmed Carbohydrate‐Functionalized Triazolylidene Iridium Complexes: Hydrogenation Catalysis in Water with Asymmetric Induction
title_short Carbohydrate‐Functionalized Triazolylidene Iridium Complexes: Hydrogenation Catalysis in Water with Asymmetric Induction
title_sort carbohydrate‐functionalized triazolylidene iridium complexes: hydrogenation catalysis in water with asymmetric induction
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9310948/
https://www.ncbi.nlm.nih.gov/pubmed/35910522
http://dx.doi.org/10.1002/cctc.202200086
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