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Ir/Thioether-Carbene, -Phosphinite, and -Phosphite Complexes for Asymmetric Hydrogenation. A Case for Comparison - imarina:5904198

Autor/s de la URV:Biosca Brull, Maria / BORRÀS NOGUERA, CARLOTA / De La Cruz Sánchez Badia, Pol / Diéguez Fernández, Montserrat / Faiges Marcos, Jorge / Pamies Ollé, Oscar
Autor segons l'article:de la Cruz-Sanchez, Pol; Faiges, Jorge; Mazloomi, Zahra; Borras, Carlota; Biosca, Maria; Pamies, Oscar; Dieguez, Montserrat
Adreça de correu electrònic de l'autor:maria.biosca@urv.cat
jorge.faiges@urv.cat
pol.delacruzsanchez@estudiants.urv.cat
pol.delacruzsanchez@estudiants.urv.cat
jorge.faiges@urv.cat
oscar.pamies@urv.cat
montserrat.dieguez@urv.cat
Identificador de l'autor:0000-0002-9116-6318
0000-0002-2352-8508
0000-0002-8450-0656
Any de publicació de la revista:2019
Tipus de publicació:Journal Publications
ISSN:02767333
Referència de l'ítem segons les normes APA:de la Cruz-Sanchez, Pol; Faiges, Jorge; Mazloomi, Zahra; Borras, Carlota; Biosca, Maria; Pamies, Oscar; Dieguez, Montserrat (2019). Ir/Thioether-Carbene, -Phosphinite, and -Phosphite Complexes for Asymmetric Hydrogenation. A Case for Comparison. Organometallics, 38(21), 4193-4205. DOI: 10.1021/acs.organomet.9b00514
Referència a l'article segons font original:Organometallics. 38 (21): 4193-4205
Resum:© 2019 American Chemical Society. We studied for the first time the potential of novel and simple Ir/thioether-NHC complexes in the asymmetric hydrogenation of unfunctionalized olefins and cyclic β-enamides. For comparison, we prepared and applied the analogues thioether-phosphinite/phosphite complexes. We found that the efficiency of the new Ir/thioether-NHC catalyst precursors varies with the type of olefin. Thus, while the Ir/thioether-NHC catalyst precursors provided lower catalytic performance than their related Ir/thioether-P complexes in the hydrogenation of olefins lacking a coordinating group, the catalysts had similar good performance for the reduction of functionalized olefins (e.g., tri- and disubstituted enol phosphonate derivatives). Catalytic results together with the studies of the reactivity toward H2 indicated that the thioether-carbene design favors the formation of inactive trinuclear species, which are responsible for the low activities obtained with these carbene-type catalysts. Nevertheless, this catalyst deactivation can be avoided by using functionalized olefins such as enol phosphonates. We also report the discovery of simple-to-synthesize Ir/thioether-P catalysts containing a simple backbone that gave high enantioselectivities for some trisubstituted olefins, some challenging 1,1′-disubstituted olefins, and cyclic β-enamides.
DOI de l'article:10.1021/acs.organomet.9b00514
Versió de l'article dipositat:info:eu-repo/semantics/acceptedVersion
Departament:Química Física i Inorgànica
Química Física i Inorgànica
URL Document de llicència:https://repositori.urv.cat/ca/proteccio-de-dades/
Àrees temàtiques:Química
Physical and theoretical chemistry
Organic chemistry
Materiais
Inorganic chemistry
Engenharias ii
Ciências biológicas ii
Ciências agrárias i
Chemistry, organic
Chemistry, inorganic & nuclear
Astronomia / física
Paraules clau:Selective catalysts
Oxazoline ligands
N-heterocyclic carbenes
Molecular-orbital methods
Mixed phosphorus/sulfur ligands
Minimally functionalized olefins
Iridium-catalyzed hydrogenation
Imidazolium salts
Basis-sets
Ab-initio
Entitat:Universitat Rovira i Virgili
Data d'alta del registre:2025-01-27
Pàgina inicial:4193
Pàgina final:4205
Volum de revista:38
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