27948-27-2

Upstream product

• 932-88-7 1-iodo-2-phenylethyne 
• 292638-85-8 acrylic acid methyl ester 
• 71022-74-7 (E)-1,2-diiodostyrene 
• 100-42-5 styrene 
• 6213-87-2 methyl (2E)-3-bromoacrylate 
• 536-74-3 phenylacetylene 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 2579-22-8 Phenylpropargyl aldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 6213-88-3 (E)-methyl 3-iodoacrylate 
• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 
• 412304-80-4 methyl 5-phenylpenta-2,4-diynoate 

Downstream Products

• 24595-58-2 5-phenylpent-4-yn-1-ol 
• 27948-28-3 (E)-5-phenyl-pent-2-en-4-ynoic acid 

Relevant academic research and scientific papers

Total Synthesis of Asparenydiol by Two Sonogashira Cross-Coupling Reactions Promoted by Supported Pd and Cu Catalysts

Asparenydiol, which is an important natural compound with potential pharmacological activities, was synthesized through two Sonogashira cross-coupling reactions catalyzed by supported Pd and Cu catalysts and by a Mitsunobu etherification. The optimization

Palladium-Catalyzed Vinylation of Acetylenic Iodides under Solid-Liquid Phase-Transfer Conditions

Methyl (E)-enynoates and (E)-enynones can be obtained in fair yields by Pd-catalyzed vinylation of 1-iodo-1-alkynes under solid-liquid phase-transfer conditions (potassium carbonate or sodium carbonate/tetrabutylammonium chloride).

Phosphine-Mediated [4 + 3] Annulation of Diynoates and 2-Arylidene Indane-1,3-diones: Access of Indeno[1,2- b]oxepin-4-ylidenes and beyond

A novel unprecedented triphenylphosphine-mediated [4 + 3] annulation reaction of 2-benzylidene indane-1,3-diones and -diynoates through initial phosphine α-addition was discovered and found to result in biologically interesting indeno[1,2-b]oxepin-4-ylidenes in up to 75% yield. The seven-membered separable Z and E isomeric oxepins were confirmed using single-crystal X-ray diffraction.

Chemoselective Biohydrogenation of Alkenes in the Presence of Alkynes for the Homologation of 2-Alkynals/3-Alkyn-2-ones into 4-Alkynals/Alkynols

The chemoselective hydrogenation of alkenes in the presence of alkynes is a very challenging transformation to achieve with traditional chemical methods. The development of an effective procedure to perform this transformation would enrich the tool-kit available to organic chemists for the development of useful synthetic routes, and the creation of novel structural motifs. The reduction of activated alkene bonds by ene-reductases (ERs) is completely chemoselective, because of the mechanism of the reaction. Thus, we investigated the use of ERs belonging to the Old Yellow Enzyme family for the reduction of α,β-unsaturated aldehydes with a conjugated C≡C triple bond at the γ position. This reaction was exploited as the key step for the development of an effective homologation route to convert aryl and alkyl substituted propynals and butynones into 4-alkynals and 4-alkynols, avoiding some troublesome or hazardous steps of known synthetic routes. (Figure presented.).

Cobalt-Catalyzed ortho-C?H Functionalization/Alkyne Annulation of Benzylamine Derivatives: Access to Dihydroisoquinolines

A practical picolinamide-directed C?H functionalization/alkyne annulation of benzylamine derivatives enabling access to the previously elusive 1,4-dihydroisoquinoline skeleton was developed using molecular O2 as the sole oxidant and Co(OAc)2 as precatalyst. The method is compatible with both internal and terminal alkynes and shows high versatility and functional-group tolerance. Furthermore, full preservation of enantiopurity is observed when using non-racemic α-substituted benzylamine derivatives. Kinetic analysis of the reagents and catalyst, labeling experiments, and the isolation and identification of catalytically competent Co-complexes revealed important insights about the mechanism.

Chemo-, regio- and stereoselective tricyclohexylphosphine-catalyzed [3+2] cycloaddition of enynes with [60]fullerene initiated by 1,4-michael addition: Synthesis of cyclopenteno[60]fullerenes and their electrochemical properties

Herein we demonstrate a tricyclohexylphosphine-catalyzed cycloaddition of (E)- or (Z)-alkyl 5-substituted phenylpent-2-en-4-ynoates with [60]fullerene to give cyclopentenofullerenes in good to excellent yields, through initial chemo- and regioselective 1,4-addition of phosphines at the b-carbon of the enyne substrates. The nucleophilic addition pattern of P (cHx)3 is found to be different from that of Gilman or Grignard reagents toward the studied enynes. The resulting cyclopentenofullerenes, characterized with spectrometric methods and single crystal X-ray diffraction analysis, exhibit comparable or higher LUMO energy levels than a typical n-type material, [6,6]-phenyl-C61-butyric acid methyl ester (PCBM).

Synthesis of substituted acetylenes, aryl-alkyl ethers, 2-alkene-4-ynoates and nitriles using heterogeneous mesoporous Pd-MCM-48 as reusable catalyst

Pd-MCM-48 has been employed as a heterogeneous catalyst for the synthesis of substituted acetylenes via Sonogashira reactions under copper and amine-free reaction conditions. In addition, the catalyst exhibited excellent regioselectivity for primary alcohols towards C-O coupling leading to formation of alkyl-aryl ethers in high yields. A green procedure for the stereoselective synthesis of 2-alkene-4-ynoates and nitriles from the reactions of vic-(E)-diiodoalkenes with activated alkenes has also been demonstrated using Pd-MCM-48 catalyst. The catalyst was easily recovered from the reaction mixture by filtration and reused for at least six times with minimal loss of activity.

A new route to the synthesis of (E)-and (Z)-2-alkene-4-ynoates and nitriles from vic-diiodo-(E)-alkenes catalyzed by Pd(0) nanoparticles in water

An efficient procedure for the stereoselective synthesis of (E)- and (Z)-2-alkene-4-ynoates and -nitriles by a simple reaction of vic-diiodo-(E)-alkenes with acrylic esters and nitriles catalyzed by in situ prepared Pd(0) nanoparticles in water has been d

Palladium-catalyzed oxidative alkynylation of alkenes via C-C bond cleavage under oxygen atmosphere

(Matrix presented) Palladium-catalyzed oxidative alkynylation of alkenes using tert-propargylic alcohols as alkynylation reagents via C-C bond cleavage under an oxygen atmosphere affords the corresponding ene-yne compounds.