title: Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles.
abstract: The Pd(0)-catalyzed allylic cross-coupling of homoallylic tosylate substrates using boronic acids and pinacol esters is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (quinox) as a ligand and is performed at ambient temperature. The scope of the reaction is broad in terms of both the boronate transmetalating reagent and the substrate and includes secondary tosylates. Mechanistic studies support an alkene-mediated S(N)2-type stereoinvertive oxidative addition of unactivated primary and secondary alkyl tosylates.
authors: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA.
authors: Benjamin J
authors: BJ
authors: Stokes
authors: Susanne M
authors: SM
authors: Opra
authors: Matthew S
authors: MS
authors: Sigman
mesh_terms: D002384:Catalysis; D010165:Palladium / Q000737:chemistry*; D013696:Temperature
chemical_list: D010165:Palladium