116156-19-5

Upstream product

• 103-64-0 bromostyrene 
• 768-60-5 4-methoxyphenylacetylen 
• 2227-57-8 3-(4-methoxyphenyl)propynoic acid 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 32117-52-5 1-(1-(4-methoxyphenyl)ethylidene)-2-tosylhydrazine 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 3989-14-8 (4-methoxyphenylethynyl)trimethylsilane 
• 100-42-5 styrene 
• 33675-41-1 1-bromo-2-(4-methoxyphenyl)acetylene 
• 14371-10-9 (E)-3-phenylpropenal 
• 90766-67-9 1,1-dibromo-4-phenyl-1,3-butadiene 
• 696-62-8 para-iodoanisole 
• 1608-03-3 (E)-but-1-en-3-yn-1-ylbenzene 

Downstream Products

• 120999-53-3 (E)-2-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-4-phenyl-but-3-enal 
• 107909-19-3 2-(4-Methoxy-phenyl)-5-phenyl-cyclopent-2-enone 
• 116156-14-0 4-(4-Methoxy-phenyl)-3-((E)-styryl)-5H-furan-2-one 
• 84066-68-2 (3E)-1-(4-methoxyphenyl)-4-phenylbut-3-en-1-one 
• 144774-54-9 (Z)-1-(4-methoxyphenyl)-4-phenylbut-2-ene-1,4-dione 
• 117535-79-2 (E)-1-(4-methoxyphenyl)-4-phenylbut-3-en-2-one 

Relevant academic research and scientific papers

Electro-alkynylation: Intramolecular Rearrangement of Trialkynylorganoborates for Chemoselective C(sp2)-C(sp) Bond Formation

An alternative and complementary transformation for the synthesis of aryl- and heteroaryl-substituted alkynes is presented that relies on a chemoselective electrocoupling process. Tetraorganoborate substrates were logically designed and simply accessed by transmetalations using readily or commercially available organotrifluoroborate salts.

A polystyrene supported [PdCl-(SeCSe)] complex: A novel, reusable and robust heterogeneous catalyst for the Sonogashira synthesis of 1,2-disubstituted alkynes and 1,3-enynes

3,5-Bis((phenylselanyl)methyl)phenol has been synthesized as a novel SeCSe pincer type pre-ligand from commercially available 5-hydroxy isophthalic acid through a multistep synthesis. Then, a polystyrene-supported SeCSe pincer ligand and its corresponding palladium complex were prepared and characterized using different techniques including FT-IR, SEM/EDX, TG/DTG, and XPS. The amount of palladium incorporated into the polymer matrix as determined by ICP analysis was obtained to be 3.64 wt% (0.34 mmol g-1). The PS[PdCl-SeCSe] catalytic activity has been evaluated in the Sonogashira coupling of diverse aryl halides with aromatic and aliphatic terminal alkynes. It was also noted that less reactive and inexpensive aryl bromides and aryl chlorides have been successfully cross-coupled with terminal alkynes using low catalyst loading. Moreover, the developed methodology is effective for the stereoselective preparation of substituted 1,3-enynes.

One-Pot Domino Synthesis of Diarylalkynes/1,4-Diaryl-1,3-diynes by [9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene] (Xantphos)–Copper(I) Iodide–Palladium(II) Acetate-Catalyzed Double Sonogashira-Type Reaction

The low loading combination of the complex [9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene] (Xantphos)copper(I) iodide and simple ligand-free palladium(II) acetate was found to be efficient for the domino synthesis of diarylalkynes by the reaction of aryl halides with trimethylsilylethynylene or bis(trimethylsilyl)acetylene in a single-step procedure. The unsymmetrical diarylalkynes can be obtained through a one-pot two-step approach. The reactions of aryl bromides with 1,4-bis(trimethylsilyl)butadiyne also furnished the corresponding 1,4-diaryl-1,3-diynes in a similar fashion. This route to diarylalkynes and 1,4-diaryl-1,3-diynes is complementary to previously reported synthetic procedures. (Figure presented.).

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

Copper-catalyzed aerobic oxidative transformation of ketone- Derived N-tosyl hydrazones: An entry to alkynes

A novel strategy involving Cu-catalyzed oxidative transformation of ketone-derived hydrazone moiety to various synthetic valuable internal alkynes and diynes has been developed. This method features inexpensive metal catalyst, green oxidant, good functional group tolerance, high regioselectivity and readily available starting materials. Oxidative deprotonation reactions were carried out to form internal alkynes and symmetrical diynes. Cross-coupling reactions of hydrazones with halides and terminal alkynes were performed to afford functionalized alkynes and unsymmetrical conjugated diynes. A mechanism proceeding through a Cu-carbene intermediate is proposed for the CC triple bond formation.

Ligand-accelerating low-loading copper-catalyzed effective synthesis of (E)-1,3-enynes by coupling between vinyl halides and alkynes performed in water

The useful conjugated enynes could be easily prepared via low-loading (0.0001 mol %) copper-catalyzed coupling between vinyl halides and terminal alkynes. It is noteworthy that this reaction could be preformed in water without using any co-solvents and the desired 1,3-enynes could be obtained with good yields. In the catalytic reaction, ligand-acceleration effect was markable.

Enyne synthesis through a modified Sonogashira cross-coupling reaction catalyzed by cyclopalladated complexes

A series of conjugated enynes were successfully synthesized by the palladacycle-catalyzed modified Sonogashira cross-coupling reaction of β-bromostyrene and terminal alkynes. The reaction proceeds smoothly in DMSO at 40 °C to give the corresponding produc

Highly regio- and stereoselective synthesis of 1,3-enynes from unactivated ethylenes via palladium-catalyzed cross-coupling

An efficient procedure for regio- and stereoselective synthesis of a series of conjugated enynes by a simple Pd-catalyzed cross-coupling reaction of unactivated ethylenes and ethynyl bromide has been developed. The reaction proceeds smoothly in DMF to give the corresponding products in good to excellent yields. The protocol can tolerate a broad range of functional groups on the substrates.

Palladium-free synthesis of conjugated enynes by direct olefination of terminal alkynes using vinyl bromides

A series of conjugated enynes were successfully synthesized by the direct copper-catalyzed coupling reaction of vinyl bromides and alkynes. The reaction proceeds smoothly in DMF at 110 °C to give the corresponding products in good to excellent yields. The protocol is tolerant to a broad range of functional groups on the substrates. Moreover, the products were furnished as specific E isomers, as the stereochemistry of the vinyl bromides was retained.

Carbonylation of Enynes under Hydroformylation Conditions Catalyzed by Rhodium Carbonyl. A New Method for Synthesis of Cyclic Enones

The reactivities of 1-buten-3-yne derivatives toward hydroformylation were studied using a rhodium catalyst.Unexpectedly, cyclopentenone derivatives were obtained in moderate yields together with formyl-substituted dienes and unsaturated lactones.This rea