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Conformational Preferences of a Tropos Biphenyl Phosphinooxazoline-a Ligand with Wide Substrate Scope
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
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2016 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 6, no 3, 1701-1712 p.Article in journal (Refereed) PublishedText
Abstract [en]

Excellent enantioselectivities are observed in palladium-catalyzed allylic substitutions of a wide range of substrate types and nucleophiles using a bidentate ligand composed of oxazoline and chirally flexible biaryl phosphite elements. This unusually wide substrate scope is shown by experimental and theoretical studies of its eta(3)-allyl and eta(2)-olefin complexes not to be a result of configurational interconversion of the biaryl unit, since the ligand in all reactions adopts an S-a,S configuration on coordination to palladium, but rather the ability of the ligand to adapt the size of the substrate-binding pocket to the reacting substrate. This ability also serves as an explanation to its excellent performance in other types of catalytic processes.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2016. Vol. 6, no 3, 1701-1712 p.
Keyword [en]
palladium, allylic substitution, tropos P, N-ligands, NMR study, DFT study
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-184535DOI: 10.1021/acscatal.5b02766ISI: 000371755500038ScopusID: 2-s2.0-84960192423OAI: oai:DiVA.org:kth-184535DiVA: diva2:917389
Funder
Swedish Research Council, 621-2012-3391
Note

QC 20160406

Available from: 2016-04-06 Created: 2016-04-01 Last updated: 2016-04-06Bibliographically approved

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Bellini, RosalbaMoberg, Christina
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