Gold-catalyzed highly regioselective oxidation of C-C triple bonds without acid additives: propargyl moieties as masked α,β-unsaturated carbonyls.
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.
Lu
Biao
B
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA.
Li
Chaoqun
C
Zhang
Liming
L
D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D010084:Oxidation-Reduction
D007659:Ketones; D006046:Gold