34600-24-3

Upstream product

• 13146-23-1 copper(I) phenylacetylenide 
• 591-97-9 1-chloro-2-butene 
• 14036-57-8 Vinylessigsaeure- 
• 536-74-3 phenylacetylene 
• 563-52-0 2-chloro-3-butene 
• 3757-88-8 tributylstannylethynylbenzene 
• 4894-61-5 trans-but-2-enyl chloride 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 4784-77-4 (E/Z)-crotyl bromide 
• 74-83-9 methyl bromide 
• 4289-20-7 1-phenyl-4-penten-1-yne 

Downstream Products

• 34600-31-2 Trimethyl-(3-methyl-1-phenyl-penta-1,2,4-trienyl)-silane 

Relevant academic research and scientific papers

Copper catalyzed regioselective coupling of allylic halides and alkynes promoted by weak inorganic bases

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.

Regioselectivity of Reaction of Cuprous Acetylides with 1-Bromo-2-butene

Regioselectivity was studied of 1,4-enyne formation in reactions of σ-acetylenic complexes of copper (neutral acetylides, equilibrium hetero and homocuprates). The reaction is the most regioselective with homocuprates, and the influence of the substituents in acetylene is weak. The effect on regioselectivity of substituents in the phenyl ring of substituted phenylacetylenes was investigated.

Nickel-Catalyzed Cross-Coupling Reaction of Allyl Halides with Alkynyltins

A cross-coupling reaction of allyl halides 1 with alkynyltins 3 in the presence of "Ni(PR3)n" (R = Ph, OEt, or OPh) catalyst was carried out in THF at reflux to give 1,4-enynes.The regioselectivity of the coupling of 1f-i with 3a was investigated in the presence of various phosphorus ligands.Interestingly, prenyl (1j) and geranyl chlorides (1k) selectively reacted with 3 at the more-hindered positions of substituted η3-allylnickel intermediates 21 (M = Ni) to yield 23 and 25, respectively.Regioselectivity in these reactions may result from greater steric crowding between the phosphorus ligand and the disubstituted position in 26b than in 26a.In contrast, the palladium-catalyzed reactions of 1j and 1k with 3 selectively gave 22 and 24, respectively.Thus, the steric crowding in a Pd analogue of 26b is less than that in a Ni analogue of 26b, since Pd has a larger covalent radius than Ni.