title: Rhodium-catalyzed enantioselective silylation of arene C-H bonds: desymmetrization of diarylmethanols.
abstract: 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.
authors.affiliation: †Department of Chemistry, University of California, Berkeley, California 94720, United States.
authors.forename: Taegyo
authors.initials: T
authors.lastname: Lee
authors.affiliation: †Department of Chemistry, University of California, Berkeley, California 94720, United States.
authors.forename: Tyler W
authors.initials: TW
authors.lastname: Wilson
authors.affiliation: ‡SP Process Development AB, Technical Research Institute of Sweden, Forskargatan 20, SE-15136 Södertälje, Sweden.
authors.forename: Robert
authors.initials: R
authors.lastname: Berg
authors.affiliation: ‡SP Process Development AB, Technical Research Institute of Sweden, Forskargatan 20, SE-15136 Södertälje, Sweden.
authors.forename: Per
authors.initials: P
authors.lastname: Ryberg
authors.affiliation: †Department of Chemistry, University of California, Berkeley, California 94720, United States.
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig