34600-27-6Relevant academic research and scientific papers
Regioselectivity in coupling of allyl halides with copper acetylene complexes
Matveeva,Yerin,Kurts
, p. 1572 - 1576 (2007/10/03)
A regiselectivity of 1,4-enynes formation in reaction of σ-acetylene copper complexes (copper acetylenides, alkynyliodocuprates, dialkynylcuprates) with various allyl halides was investigated. The most selective reaction was observed between dialkynylcuprates and geranyl bromide.
Trimethylsilylphenylacetylene in C-Alkynylation Reactions
Komissarova,Aleksandrova,Stadnichuk
, p. 412 - 416 (2007/10/03)
Direction and yields of products of the reaction between phenylethynyl anions, generated from trimethylsilylphenylacetylene under the action of potassium fluoride in DMF, and C-electrophilic reagents (aliphatic and aromatic aldehydes and ketones, aliphatic and aromatic acyl chlorides, aryl halides, and alkenyl chlorides with chlorine in the allylic position) are controlled by their structure. Secondary acetylenic alcohols prepared from aromatic aldehydes, as well as their trimethylsilyl ethers, undergo uncatalyzed Meyer-Schuster rearrengement.
Nickel-Catalyzed Cross-Coupling Reaction of Allyl Halides with Alkynyltins
Cui, Dong-Mei,Hashimoto, Naoko,Ikeda, Shin-ichi,Sato, Yoshiro
, p. 5752 - 5756 (2007/10/03)
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.
