title: Copper-catalyzed extended Pummerer reactions of ketene dithioacetal monoxides with alkynyl sulfides and ynamides with an accompanying oxygen rearrangement.
abstract: The first examples of metal-catalyzed extended Pummerer reactions through the activation of sulfoxides are described. The copper-catalyzed reactions of ketene dithioacetal monoxides with alkynyl sulfides and ynamides provided a wide variety of γ,γ-disulfanyl-β,γ-unsaturated carbonyl compounds with an accompanying oxygen rearrangement. The products can be easily converted into 1,4-dicarbonyl compounds and substituted heteroaromatics. DFT calculations and mechanistic experiments revealed a new interesting stepwise addition/oxygen rearrangement mechanism.
authors: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, Japan.
authors: Kei
authors: K
authors: Murakami
authors: Junichi
authors: J
authors: Imoto
authors: Hiroshi
authors: H
authors: Matsubara
authors: Suguru
authors: S
authors: Yoshida
authors: Hideki
authors: H
authors: Yorimitsu
authors: Koichiro
authors: K
authors: Oshima
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D000480:Alkynes; D005030:Ethylenes; D007659:Ketones; D013440:Sulfides; D013454:Sulfoxides; D003300:Copper; C008223:ketene; D010100:Oxygen