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Extending the Substrate Scope of Bicyclic P-Oxazoline/Thiazole Ligands for Ir-Catalyzed Hydrogenation of Unfunctionalized Olefins by Introducing a Biaryl Phosphoroamidite Group
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2015 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 21, no 8, 3455-3464 p.Article in journal (Refereed) Published
Abstract [en]

This study identifies a series of Ir-bicyclic phosphoroamidite-oxazoline/thiazole catalytic systems that can hydrogenate a wide range of minimally functionalized olefins (including E-and Z-tri- and disubstituted substrates, vinylsilanes, enol phosphinates, tri- and disubstituted alkenylboronic esters, and alpha,beta-unsaturated enones) in high enantioselectivities (ee values up to 99%) and conversions. The design of the new phosphoroamidite-oxazoline/thiazole ligands derives from a previous successful generation of bicyclic N-phosphane-oxazoline/thiazole ligands, by replacing the N-phosphane group with a pi-acceptor biaryl phosphoroamidite moiety. A small but structurally important family of Ir-phosphoroamidite-oxazoline/thiazole precatalysts has thus been synthesized by changing the nature of the N-donor group (either oxazoline or thiazole) and the configuration at the biaryl phosphoroamidite moiety. The substitution of the N-phosphane by a phosphoroamidite group in the bicyclic N-phosphane-oxazoline/thiazole ligands extended the range of olefins that can be successfully hydrogenated.

Place, publisher, year, edition, pages
2015. Vol. 21, no 8, 3455-3464 p.
Keyword [en]
asymmetric catalysis, hydrogenation, ligand design, iridium, P ligands
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-115679DOI: 10.1002/chem.201405361ISI: 000349664300040PubMedID: 25640110OAI: oai:DiVA.org:su-115679DiVA: diva2:799701
Funder
Swedish Research CouncilStiftelsen Olle Engkvist ByggmästareSwedish Energy Agency
Note

AuthorCount:5;

Available from: 2015-03-31 Created: 2015-03-27 Last updated: 2017-12-04Bibliographically approved

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