68753-95-7Relevant academic research and scientific papers
Palladium-catalyzed cross-coupling of alkynylzincs with allylic electrophiles: An efficient and selective synthesis of stereo- and regio-defined 1,4-enynes
Qian, Mingxing,Negishi, Ei-Ichi
, p. 1789 - 1793 (2005)
Clean and high-yielding cross-coupling of alkynylzincs with allylic chlorides, bromides, or acetates exhibiting ≥ 98% regio-and stereoselectivity can be achieved by using 1 mol% of Pd(DPEphos)Cl2 and either 1:1 THF-DMF or pure DMF. This reaction provides a satisfactory route to 1,4-enynes via Pd-catalyzed alkynyl-allyl coupling. Georg Thieme Verlag Stuttgart.
Palladium-catalyzed substitution reaction of allylic derivatives with tinacetylene
Nishikawa, Toshio,Isobe, Minoru
, p. 238 - 242 (1999)
The substitution reaction of allylic derivatives (acetate, carbonate, and chloride) with tinacetylene proceeded in the presence of palladium as a catalyst to give a product having a 1-ene-4-yne system.
Copper catalyzed regioselective coupling of allylic halides and alkynes promoted by weak inorganic bases
Bieber, Lothar W.,da Silva, Margarete F.
, p. 7088 - 7090 (2008/03/11)
Allylic halides and terminal alkynes couple under CuI catalysis in DMSO or DMF solution. In most cases, sodium carbonate or bicarbonate is sufficient to promote the reaction; less reactive alkynes require catalytic amounts of DBU. Bifunctional alkynes and halides can be reacted selectively according to the stoichiometry used. Trimethylsilyl, hydroxyl, ester and halide groups are tolerated in the alkyne. Most halides react without allylic rearrangement. The method is suitable for the synthesis of functionalized enynes.
