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Asymmetric Synthesis of Alkyl Fluorides: Hydrogenation of Fluorinated Olefins
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry. University of KwaZulu-Natal, South Africa.ORCID iD: 0000-0002-1383-8246
Number of Authors: 42019 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 27, p. 9282-9287Article in journal (Refereed) Published
Abstract [en]

The development of new general methods for the synthesis of chiral fluorine-containing molecules is important for several scientific disciplines. We herein disclose a straightforward method for the preparation of chiral organofluorine molecules that is based on the iridium-catalyzed asymmetric hydrogenation of trisubstituted alkenyl fluorides. This catalytic asymmetric process enables the synthesis of chiral fluorine molecules with or without carbonyl substitution. Owing to the tunable steric and electronic properties of the azabicyclo thiazole-phosphine iridium catalyst, this stereoselective reaction could be optimized and was found to be compatible with various aromatic, aliphatic, and heterocyclic systems with a variety of functional groups, providing the highly desirable products in excellent yields and enantioselectivities.

Place, publisher, year, edition, pages
2019. Vol. 58, no 27, p. 9282-9287
Keywords [en]
alkenyl fluorides, asymmetric hydrogenation, iridium catalysis, N, P ligands, organofluorine compounds
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-171794DOI: 10.1002/anie.201903954ISI: 000476691200057PubMedID: 30995362OAI: oai:DiVA.org:su-171794DiVA, id: diva2:1345644
Available from: 2019-08-26 Created: 2019-08-26 Last updated: 2019-08-26Bibliographically approved

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