title: Pd(Quinox)-Catalyzed Allylic Relay Suzuki Reactions of Secondary Homostyrenyl Tosylates via Alkene-Assisted Oxidative Addition.
abstract: Pd-catalyzed allylic relay Suzuki cross-coupling reactions of secondary alkyl tosylates, featuring a sterically-hindered oxidative addition and precise control of β-hydride elimination, are reported. The identification of a linear free energy relationship between the relative rates of substrate consumption and the electronic nature of the substrate alkene suggests that the oxidative addition requires direct alkene involvement. A study of the effect of chain length on the reaction outcome supports a chelation-controlled oxidative addition.
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah, USA, ; Tel: +1 801-585-0774.
authors.forename: Benjamin J
authors.initials: BJ
authors.lastname: Stokes
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah, USA, ; Tel: +1 801-585-0774.
authors.forename: Amanda J
authors.initials: AJ
authors.lastname: Bischoff
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah, USA, ; Tel: +1 801-585-0774.
authors.forename: Matthew S
authors.initials: MS
authors.lastname: Sigman