110792-91-1

Upstream product

• 2579-22-8 Phenylpropargyl aldehyde 
• 1779-51-7 n-butyl(triphenyl)phosphonium bromide 
• 627-19-0 1-Pentyne 
• 64907-51-3 (E)-(5-chloropent-3-en-1-yn-1-yl)benzene 
• 925-90-6 ethylmagnesium bromide 
• 10467-10-4 ethylmagnesium iodide 
• 1483-82-5 phenylethynyl chloride 
• 104376-24-1 (E)-1-pentenylboronic acid 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 66703-03-5 trans-1-iodo-1-pentene 
• 536-74-3 phenylacetylene 

Downstream Products

• 143536-17-8 1-Phenyl-hept-1-yne-3,4-diol 
• 1618657-39-8 (E)-1-phenylhept-3-en-1-one 
• 1640005-65-7 (Z)-1-phenylhept-3-en-1-one 
• 129083-13-2 trans-1-phenyl-3-hepten-2-one 

Relevant academic research and scientific papers

Copper-Catalyzed Regioselective and Stereoselective Coupling of Grignard Reagents with Pent-1-en-4-yn-3-yl Benzoates: A Shortcut to (Z) -1,5-Disubstituted Pent-3-en-1-ynes from Accessible Starting Materials

Copper-catalyzed coupling of Grignard reagents with pent-1-en-4-yn-3-yl benzoates occurs regioselectively at the terminal alkenyl carbon rather than the alkynyl site, leading to the stereoselective formation of unexpected (Z)-1,5-disubstituted pent-3-en-1-ynes without generation of the initially expected alkenyl allene products. By using easily accessible starting materials, this reaction can provide direct access to thermodynamically unfavorable Z-configured enynes, which widely exist in many bioactive natural products, such as the anti-inflammatory components in henna.

Regioselective hydrations of 1-aryl-3-en-1-ynes using gold and platinum catalysts: Selective production of 2-en-1-ones and 3-en-1-ones

Regiocontrolled hydrations of 1-aryl-3-en-1-ynes have been accomplished with IPrAuOTf and PtCl2/CO to yield 3-en-1-ones and 2-en-1-ones efficiently; our experimental data indicates that the sizes of catalysts play an important role. This journa

Cu-catalyzed Fe-driven Csp-Csp and C sp-Csp2 cross-coupling: An access to 1,3-diynes and 1,3-enynes

An efficient Csp-Csp cross-coupling of alkynyl bromide and pinacol ester of alkynyl boronic acid catalyzed by CuFe 2O4 nanoparticles has been accomplished in dimethyl carbonate to produce unsymmetric 1,3-diynes. This protocol is also extended for the Csp-Csp2 coupling of alkynyl bromide and alkenyl boronic acid to provide conjugated 1,3-enynes. The aliphatic, aromatic, and heteroaromatic alkynes couple with various substituted alkynyl/alkenyl boronates/boronic acids by this procedure to furnish a library of 1,3-diynes and enynes in high yields. The catalyst was easily separated by an external magnet and recycled 10 times.

Enyne chlorides: Substrates for copper-catalyzed asymmetric allylic alkylation

A select few: Several prochiral enyne chlorides were employed as substrates in the title reaction using Grignard reagents as the alkylation reagents (see scheme; CuTC=copper(I) thiophenecarboxylate). Excellent 1,3 substitution regioselectivities and good to excellent enantioselectivities were obtained. The substrate scope is additionally extended to diene chlorides. Copyright

Skeletal change in the PNP pincer ligand leads to a highly regioselective alkyne dimerization catalyst

A Rh complex of a bulky diarylamino-based PNP pincer ligand is a robust catalyst for the dimerization of terminal alkynes and highly selective for the trans-enyne product. The Royal Society of Chemistry 2006.

PHASE-TRANSFER VERSION OF THE WITTIG REACTION AND ITS STEREOCHEMISTRY IN THE ALIPHATIC SERIES

Alkyltriphenylphosphonium salts react with saturated α,β-ethylenic, α,β-acetylenic, and cyclic aliphatic aldehydes when heated with solid potassium carbonate to form the corresponding alkenes with preparative yields.The reaction is cis-stereoselective with saturated aldehydes and cis-stereospecific with unsaturated aldehydes.