Chemoselective oxidation of carbon-carbon double or triple bonds to 1,2-diketones with DMSO-based reagents

Article abstract of DOI:10.1055/s-1995-4094

HBr/DMSO selectively oxidizes the double bond in (E)-1-(2-phenylethenyl)-4-(phenylethynyl)benzene (1) to 1,2-diketone 2. However, 1₂/DMSO and PdCl₂/DMSO oxidize only the triple bond in 1 to 1,2-diketone 3. A similar trend of chemoselectivity is shown for the oxidation of (E)-1,4-diphenyl-1-buten-3-yne (6) with the DMSO-based reagents.