1007597-75-2Relevant academic research and scientific papers
Copper-catalyzed extended pummerer reactions of ketene dithioacetal monoxides with alkynyl sulfides and ynamides with an accompanying oxygen rearrangement
Murakami, Kei,Imoto, Junichi,Matsubara, Hiroshi,Yoshida, Suguru,Yorimitsu, Hideki,Oshima, Koichiro
, p. 5625 - 5630 (2013/06/26)
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. Beyond Pummerer: The first examples of copper-catalyzed extended Pummerer 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 (see scheme). 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.
Syntheses of α-stannylated and α-iodinated enamides via molybdenum-catalyzed hydrostannation
Maity, Pulakesh,Klos, Manuel R.,Kazmaier, Uli
, p. 6246 - 6249 (2014/01/17)
α-Stannylated and α-iodinated enamides can easily be obtained by molybdenum-catalyzed regio- and stereoselective hydrostannation and subsequent tin-iodine exchange. These functionalized enamides are interesting building blocks for a wide range of cross-coupling reactions giving access to various types of α-substituted enamides.
Radical additions of arenethiols to ynamides for the selective synthesis of N-[(Z)-2-(Arylsulfanyl)-1-alkenyl]amides
Sato, Akinori,Yorimitsu, Hideki,Oshima, Koichiro
experimental part, p. 570 - 576 (2010/09/05)
A variety of ynamides undergo highly regio- and stereoselective radical addition of arenethiols with the aid of trie- thylborane as a radical initiator. The products, N-[-2-arylsulfanyl-1 -alkenyl]amides, can be reduced with triethyl- silane in trifluoroa
Copper-catalyzed aerobic oxidative amidation of terminal alkynes: Efficient synthesis of ynamides
Hamada, Tetsuya,Ye, Xuan,Stahl, Shannon S.
, p. 833 - 835 (2008/09/21)
A copper-catalyzed method for the preparation of ynamides has been identified that proceeds via aerobic oxidative coupling of terminal alkynes with various nitrogen nucleophiles, including cyclic carbamates, amides and ureas, and N-alkyl-arylsulfonamides and indoles. Copyright
