title: Catalytic Synthesis of "Super" Linear Alkenyl Arenes Using an Easily Prepared Rh(I) Catalyst.
abstract: Linear alkyl benzenes (LAB) are global chemicals that are produced by acid-catalyzed reactions that involve the formation of carbocationic intermediates. One outcome of the acid-based catalysis is that 1-phenylalkanes cannot be produced. Herein, it is reported that [Rh(μ-OAc)(η2-C2H4)2]2catalyzes production of 1-phenyl substituted alkene products via oxidative arene vinylation. Since C═C bonds can be used for many chemical transformations, the formation of unsaturated products provides a potential advantage over current processes that produce saturated alkyl arenes. Conditions that provide up to a 10:1 linear:branched ratio have been achieved, and catalytic turnovers >1470 have been demonstrated. In addition, electron-deficient and electron-rich substituted benzenes are successfully alkylated. The Rh catalysis provides ortho:meta:para selectivity that is opposite to traditional acid-based catalysis.
authors.affiliation: Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904, United States.
authors.forename: Michael S
authors.initials: MS
authors.lastname: Webster-Gardiner
authors.affiliation: Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904, United States.
authors.forename: Junqi
authors.initials: J
authors.lastname: Chen
authors.affiliation: Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904, United States.
authors.forename: Benjamin A
authors.identifier: 0000-0001-9607-5696
authors.initials: BA
authors.lastname: Vaughan
authors.affiliation: Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904, United States.
authors.forename: Bradley A
authors.initials: BA
authors.lastname: McKeown
authors.forename: William
authors.initials: W
authors.lastname: Schinski
authors.affiliation: Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904, United States.
authors.forename: T Brent
authors.identifier: 0000-0001-5714-3887
authors.initials: TB
authors.lastname: Gunnoe