80033-73-4

Upstream product

• 5701-81-5 buta-1,3-diynylbenzene 
• 2386-64-3 ethylmagnesium chloride 
• 1129-65-3 (hex-1-yn-1-yl)benzene 
• 925-90-6 ethylmagnesium bromide 
• 181214-48-2 [(Z)-4-bromobut-3-en-1-ynyl]benzene 
• 1817-51-2 1-phenyl-1-hexyn-3-ol 
• 917-64-6 methyl magnesium iodide 
• 75-16-1 methylmagnesium bromide 
• 536-74-3 phenylacetylene 
• 40964-63-4 1-phenyl-4-penten-1-yn-3-ol 
• 917-54-4 methyllithium 
• 23675-67-4 (4-methylpent-4-en-1-yn-1-yl)benzene 

Relevant academic research and scientific papers

Iron(III)-Catalyzed Hydration of Unactivated Internal Alkynes in Weak Acidic Medium, under Lewis Acid-Assisted Br?nsted Acid Catalysis

Alkylarylalkynes are converted with full regioselectivity into the corresponding arylketones by formal hydration of the triple bond under weak acidic conditions, at times and temperatures (≤95 °C) comparable to those used for terminal alkynes. The process catalyzed by Fe2(SO4)3nH2O in glacial acetic acid exhibits good functional group compatibility, including that with bulky triple bond substituents, and can be extended to the one-pot transformation of aryltrimethylsilylacetylenes into acetyl derivatives via a desilylation-hydration sequence. The overall reactivity pattern along with proton affinity data indicate that the triple bond is activated by proton transfer rather than by π-interaction with the metal ion. This mechanistic feature, at variance with that of noble metal catalysts, accounts for the total regioselectivity and the insensitivity to steric hindrance exhibited by the Fe2(SO4)3nH2O/AcOH catalytic system. (Figure presented.).

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.

A facile preparation of geometrically pure alkenyl, alkynyl, and aryl conjugated Z-alkenes: Stereospecific synthesis of bombykol

Ni- and Pd-catalyzed cross coupling reactions of 2-alkenyl, 2-alkynyl, and 2-aryl substituted (1Z)-1-bromoalkene with alkyl Grignard reagents gave 1-alkyl substituted (1Z,3E)-diene, (1Z)-en-3-yne, and (1Z)-2-arylethene, each in good yield. When (trimethylsilyl)-methylmagnesium chloride was used as the Grignard reagent, conjugated Z-allylsilane was produced. Bombykol, (10E, 12Z)-10,12-hexadecadien-1-ol, a sex pheromone of female moss, Bombyx mori, was synthesized stereospecifically. 2000 Elsevier Science Ltd.

A study of the reactions of 1,3-diynes with organo-cuprates and -argentates

1,3-Diynes HCC-CC-R' (1, R'= H or Ph) are converted by cuprates M' (R = alkyl; Y = Cl, Br or R; M'= Li, MgCl or MgBr) into a mixture of C-R'>M' (2) and C-R'>M' (3).When R is n-alkyl, adducts 2 are the major pr

Organocuprate-Induded Coupling of Propargyl or Enyne Alcohols Using (Methylphenylamino)tributylphosphonium Iodide. Regiocontrolled Synthesis of Allenes and Conjugated Enynes

Regioselective synthesis of allenes is directly achieved via organocuprate-mediated γ-coupling of propargyl alcohols by using the title reagent (1). Alternatively, the coupling between 1,4-enyn-3-ols and alkyllithium affords the conjugated Z enynes regio-