134889-85-3

Upstream product

• 124-38-9 carbon dioxide 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 21788-36-3 (Z)-methyl 2-bromo-3-phenylacrylate 
• 103-26-4 Methyl cinnamate 
• 59106-33-1 (Z)-ethyl 2-bromo-3-phenylprop-2-enoate 
• 6738-06-3 phenylethynylmagnesium bromide 
• 201413-00-5 ethyl (E)-2-phenylacetylenyl-3-phenylacrylate 

Downstream Products

• 53949-11-4 γ-phenyl-α-phenylmethylene-Δ^β,γ-butenolide 

Relevant academic research and scientific papers

One-pot and regioselective synthesis of functionalized γ-lactams via a metal-free sequential Ugi 4CR/Intramolecular 5-exo-dig cyclization reaction

A new one-pot and regioselective synthesis of functionalized γ-lactams by a metal-free Ugi 4CR/intramolecular 5-exo-dig cyclization sequence under mild conditions has been developed. The reaction of propenoic acids, aldehydes, amines, and isocyanides produced γ-lactams regioselectively in 72–89percent yields via sequential Ugi 4CR/intramolecular 5-exo-dig cyclization reaction in the presence of Cs2CO3.

Studies on the transition metal-catalyzed synthesis of variously substituted (E)-3-[1-(aryl)methylidene]- and (E)-3-(1-alkylidene)-3H-furan-2-ones

5-Aryl and 5-alkyl substituted (E)-3-[1-(aryl)methylidene]- and (E)-3-(1-alkylidene)-3H-furan-2-ones, (E)-9, have been selectively synthesized by cyclization of the corresponding (E)-2-(1-alkynyl)-3-aryl/alkylpropenoic acids, (E)-11, in the presence of AgNO3 or Pd-catalysts such as trans-di(μ-acetato)bis[(di-o-tolylphosphino)benzyl]dipalla-dium(II) or that constituted of a mixture of Et3N and PdCl2(PhCN)2 or PdCl2(CH3CN)2. in a 3:1 molar ratio, respectively. A representative (E)-5-aryl-3-[1-(aryl)methylidene]-3H-furan-2-one, i.e. (E)-9i, has been also prepared by a tandem process involving a Pd(0)- and Cu(I)-catalyzed cross-coupling reaction between an 1-alkyne and a (Z)-3-aryl-2-bromopropenoic acid followed by a catalytic intramolecular oxypalladation of the resulting cross-coupled product. However, when this same approach was used to prepare an (E)-5-alkyl-3-[1-(aryl)methylidene]-3H-furan-2-one, i.e. (E)-9j, a mixture of (E)-9j and the corresponding (E)/(Z)-5-(1-alkylidene)-3-(aryl)methyl-5H-furan-2-one, i.e. (E)/(Z)-20, was obtained. Finally, in an attempt to prepare an (E)-4-alkyl-5-aryl-3-[1-(aryl)methylidene]-3H-furan-2-one, i.e. (E)-14a, by a tandem process involving the intramolecular oxypalladation of an (E)-enynoic acid, (E)-11, followed by a cross-coupling reaction of the resulting compound with aryl iodide, a (Z)-5-(1-alkynyl)-4-aryl-3-arylmethyl-5H-furan-2-one, i.e. (Z)-22, has been stereoselectively obtained.

Activation of Carbon Dioxide: Nickel-Catalyzed Electrochemical Carboxylation if Diynes

The simualtaneous activation of carbon dioxide and diynes by electrogenerated LNi(0) complexes (L=bpy, pentamethyldiethylenetriamine: PMDTA) enables the selective incorporation of one molecule of CO2 into the unsaturated systems and the preparative-scale

First Example of Direct Carbon Dioxide Incorporation into 1,3-Diynes: A Highly Regio- and Stereo-selective Nickel-catalysed Electrochemical Reaction

The electrosynthesis of 2-vinylidene-3-yne carboxylic acids from carbon dioxide and substituted 1,3-diynes is catalysed by a nickel-triamine complex and results in a regio- and stereo-selective addition to one triple bond.