130248-54-3

Upstream product

• 768-60-5 4-methoxyphenylacetylen 
• 1066-54-2 trimethylsilylacetylene 
• 159351-36-7 1-(4-methoxyphenyl)-3-(trimethylsilyl)prop-2-yn-1-ol 
• 4526-07-2 1,4-bis(trimethylsilyl)-1,3-butadiyne 
• 22779-05-1 1,4-bis(4-methoxyphenyl)-1,3-butadiyne 
• 33675-41-1 1-bromo-2-(4-methoxyphenyl)acetylene 
• 558-13-4 carbon tetrabromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 82731-79-1 diethyl[(trimethylsilyl)acetylenyl]aluminum 
• 61926-37-2 1-(iodoethynyl)-4-methoxybenzene 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 60512-57-4 1-(2,2-dibromovinyl)-4-methoxybenzene 
• 99048-48-3 1‐(4‐methoxyphenyl)‐3‐(trimethylsilyl)prop‐2‐yn‐1‐one 
• 405064-51-9 (4,4-dibromo-3-(4-methoxyphenyl)but-3-en-1-yn-1-yl)trimethylsilane 

Downstream Products

• 1258456-66-4 C₁₆H₁₃F₃O₄ 
• 1318244-92-6 C₁₅H₁₆O₂ 
• 1611483-83-0 4-(chlorobuta-1,3-diyn-1-yl)methoxybenzene 

Relevant academic research and scientific papers

Scope and limitations of the intermolecular furan-yne cyclization

Different types of alkynes were reacted with 2,5-disubstituted furans in order to evaluate the scope of the intermolecular furan-yne reaction. With ethynyl aryl ethers as starting materials, 2-phenoxy phenols were accessible in moderate to good yields. A different reaction mode was observed for alkynes bearing electron-withdrawing substituents. For these starting materials a cis-selective hydroarylation took place in an anti-Markovnikov fashion in excellent yields. 1,2-Diynes turned out to be suitable starting materials as well. Due to the second alkynyl moiety, after an initial phenol synthesis, a subsequent hydro-alkoxylation by the newly formed phenolic oxygen gives access to benzofurans in a tandem process.

Catalytic Cyclotrimerization Pathway for Synthesis of Selaginpulvilins C and D: Scope and Limitations

A facile and unified approach to the main selaginpulvilin's framework was achieved by catalytic [2 + 2 + 2]-cyclotrimerization of a triyne with monosubtituted alkynes. The reaction proceeded with high "ortho"selectivity by using Wilkinson's catalyst (RhCl

Unraveling the Mechanism of 1,3-Diyne Cross-Metathesis Catalyzed by Silanolate-Supported Tungsten Alkylidyne Complexes

The benzylidyne complex [PhC≡W{OSi(OtBu)3}3] (1) catalyzed the cross-metathesis between 1,4-bis(trimethylsilyl)-1,3-butadiyne (2) and symmetrical 1,3-diynes (3) efficiently, which gave access to TMS-capped 1,3-diynes RC≡C?C≡CSiMesub

Ligand-Controlled Regiodivergent Nickel-Catalyzed Hydrocyanation of Silyl-Substituted 1,3-Diynes

A regiodivergent nickel-catalyzed hydrocyanation of 1-aryl-4-silyl-1,3-diynes is reported. When appropriate bisphosphine and phosphine-phosphite ligands are applied, the same starting materials can be converted into two different enynyl nitriles with good

Chemoselective Cobalt(I)-Catalyzed Cyclotrimerization of (Un)Symmetrical 1,3-Butadiynes for the Synthesis of 1,2,4-Regioisomers

The cobalt(I)-catalyzed cyclotrimerization of (un)symmetrical 1,4-disubstituted 1,3-butadiynes is presented. In the case of unsymmetrical 1,3-butadiynes, this reaction can generate eight 1,2,4-substituted and four 1,3,5-substituted isomers. A single 1,2,4-substituted isomer was formed in excellent yields (up to 99%) and exclusive regioselectivities (>99:1) when symmetrical or a 1,3-butadiyne with an aryl or alkyl substituent and a trimethylsilyl group were applied. A large number of products accepting a wide variety of functional groups were synthesized.

Highly efficient synthesis of unsymmetrical 1,3-diynes from organoalane reagents and alkynyl bromides mediated by a nickel catalyst

Highly efficient and simple cross-coupling reactions of alkynylbromides with organoalane reagents for the synthesis of unsymmetrical 1,3-diynes derivatives using Ni(OAc)2 (2-5 mol%)/(o-furyl)3P (4-10 mol%) as a catalyst are reported. Excellent yields (up to 94%) were obtained for a wide range of substrates at rt or 60 °C for 2-3 h in Et2O or toluene.

Control of the Regioselectivity in Cobalt- versus Ruthenium-Catalyzed Alder-ene Reaction of Unsymmetrical 1,3-Diynes

The Alder-ene reaction of trialkylsilyl-substituted 1,3-butadiynes with terminal alkenes was investigated utilizing a cobalt-based catalyst, and the results were compared with Alder-ene rections catalyzed by the [CpRu(H3CCN)3]PF6 catalyst. Obviously, the two catalysts gave complementary results of yn-dienes differing in the site where the new carbon-carbon bond was formed. Of particular interest are observations concerning the double bond migration within the alkene component. While simple alkenes gave exclusively the E-configuration, the application of 3-buten-1-ol resulted in the corresponding Z-double bond, indicating that the hydroxyl group acts as donor coordinating to the cobalt center and thereby altering the reaction pathway.

Syntheses of trifluoroethylated unsymmetrical 1,3-diynes by using 1,1-dichloro-2,2,2-trifluoroethane

Copper-mediated reaction of terminal 1,3-diynes with 1,1-dichloro-2,2,2-trifluoroethane (CF3CHCl2) using ethanolamine as ligand gave trifluoroethylated unsymmetrical 1,3-diynes in moderate to good yields. The reaction were carried out under mild conditions, and were easy to operate. Aryl groups with weak electron-withdrawing group or electron-donating group, and alkyl substitutents at terminal 1,3-diynes were tolerated. Synthesis of a trifluoroethylated conjugated triyne by using this method was demonstrated. Further transformation of the trifluoroethylated unsymmetrical 1,3-diyne to provide trifluoroethyl-substituted 1,2,3-triazole and isoxazole as application examples were successfully realized.

Air-stable (phenylbuta-1,3-diynyl)palladium(II) complexes: Highly active initiators for living polymerization of isocyanides

A family of air-stable (phenylbuta-1,3-diynyl)palladium(II) complexes were designed and prepared in a facile synthetic procedure. Their structures were characterized by 1H and 13C NMR, MS, and X-ray analysis. These Pd complexes were

Chiral propargyl alcohols via the enantioselective addition of terminal Di- and triynes to aldehydes

The enantioselective addition of di- and triynes to aldehydes is presented, including the first examples of an asymmetric triyne addition. Modification of the Carreira alkynylation protocol shows that addition of diynes and triynes to α-branched aldehydes can be complete in as little as 4 h, and these reactions give good yields and enantioselectivities (up to 98% ee) for di- and triynes tested (aryl, alkyl, and silyl). It is shown for two cases (20 and 24) that products of this asymmetric addition reaction can undergo further manipulation (desilylation and triazole formation) without affecting the enantiopurity.