title: Gold-catalyzed highly regioselective oxidation of C-C triple bonds without acid additives: propargyl moieties as masked α,β-unsaturated carbonyls.
abstract: Gold-catalyzed intermolecular oxidations of internal alkynes have been achieved with high regioselectivities using 8-alkylquinoline N-oxides as oxidants and in the absence of acid additives. Synthetically versatile α,β-unsaturated carbonyls are obtained in good to excellent yields and with excellent E-selectivities. A range of functional groups such as THP, MOMO, N(3), OTBS, and N-Boc are tolerated. This reaction allows α,β-unsaturated carbonyls to be masked as propargyl moieties, thus offering a practical solution to compatibility issues with these functional groups likely encountered in syntheses of complex structures.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA.
authors.forename: Biao
authors.initials: B
authors.lastname: Lu
authors.forename: Chaoqun
authors.initials: C
authors.lastname: Li
authors.forename: Liming
authors.initials: L
authors.lastname: Zhang
mesh_terms: D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D007659:Ketones; D006046:Gold