title: Synthesis of trisubstituted alkenes via direct oxidative arene-alkene coupling.
abstract: The use of an inorganic oxidant with an acetic acid/acetonitrile solvent combination has been identified as optimal for direct arene/1,2-disubstituted alkene oxidative couplings, providing an efficient route to trisubstituted alkenes. The acetonitrile cosolvent dramatically accelerates the rate of reaction, and an insoluble inorganic oxidant limits unwanted oxidation of substrates. The scope of this procedure is illustrated with arenes and alkenes containing electron-donating and -withdrawing substituents resulting in a general synthetic strategy to trisubstituted alkenes. In situ ESI-MS analysis of the reaction components has identified the key Pd intermediates in the Fujiwara-Moritani catalytic cycle.
authors.affiliation: School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
authors.forename: Roderick C
authors.initials: RC
authors.lastname: Jones
authors.forename: Michał
authors.initials: M
authors.lastname: Gałęzowski
authors.forename: Donal F
authors.initials: DF
authors.lastname: O'Shea
mesh_terms: D019342:Acetic Acid / Q000737:chemistry; D000097:Acetonitriles / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000097:Acetonitriles; D000475:Alkenes; D019342:Acetic Acid; C032159:acetonitrile