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Rhodium-Catalyzed Enantioselective Silylation of Arene C–H Bonds: Desymmetrization of Diarylmethanols
University of California, US.
University of California, US.
RISE, SP – Sveriges Tekniska Forskningsinstitut, SP Process Development, Katalys.
RISE, SP – Sveriges Tekniska Forskningsinstitut.
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2015 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 137, no 21, p. 6742-6745Article in journal (Refereed) Published
Abstract [en]

We report a Rh-catalyzed, enantioselective silylation of arene C–H bonds directed by a (hydrido)silyl group. (Hydrido)silyl ethers that are formed in situ by hydrosilylation of benzophenone or its derivatives undergo asymmetric C–H silylation in high yield with excellent enantioselectivity in the presence of [Rh(cod)Cl]2 and a chiral bisphosphine ligand. The stereoselectivity of this process also allows enantioenriched diarylmethanols to react with site selectivity at one aryl group over the other. Enantioenriched benzoxasiloles from the silylation process undergo a range of transformations to form C–C, C–O, C–I, or C–Br bonds.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2015. Vol. 137, no 21, p. 6742-6745
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:ri:diva-13636DOI: 10.1021/jacs.5b03091OAI: oai:DiVA.org:ri-13636DiVA, id: diva2:1033937
Available from: 2016-10-10 Created: 2016-10-10 Last updated: 2019-07-09Bibliographically approved

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