103606-73-1

Upstream product

• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 107-19-7 propargyl alcohol 
• 103-64-0 bromostyrene 
• 110295-96-0 trans-styryl phenyl telluride 
• 108162-13-6 (E)-1-butyltelluro-2-phenylethene 
• 67502-64-1 bis-(E)-β-styryl selenide 
• 139926-43-5 (E,E)-bis(2-phenylethenyl)telluride 
• 5272-36-6 3-trimethylsilyl-2-propyn-1-ol 

Downstream Products

• 1608-03-3 (E)-but-1-en-3-yn-1-ylbenzene 
• 501098-89-1 (E)-5-phenylpent-4-en-2-ynal 
• 1429205-50-4 (2Z,4E)-5-phenyl-2-((trimethylsilyl)ethynyl)penta-2,4-dien-1-ol 
• 1606590-27-5 C₁₉H₁₄O₂ 
• 235094-53-8 7-phenyl-6-penten-4-yne-1,3-diol 3-dihydropyranyl ether 
• 103240-57-9 5-phenyl-4-penten-2-yn-1-yl acetate 

Relevant academic research and scientific papers

Regiocontrol of the palladium-catalyzed tin hydride addition to Z-enynols: Remarkable Z-directing effects

(Figure Presented) Palladium-catalyzed hydrostannation of substituted Z- and E-enynols is discussed and compared. The regioselectivity of the H-Sn bond addition was found to be controlled by the geometry of the double bond (Z- or syn-directing effect) rather than the nature of its substituents, Exclusively α-vinyl stannanes were obtained from Z-enynols having various substituents on the double bond regardless of their electronic, steric, or chelating natures.

Stereoselective preparation of conjugated E-enynes from E-vinylic tellurides and terminal alkynes via Sonogashira cross-coupling

E-Vinylic tellurides undergo a direct cross-coupling reaction with terminal alkynes In the presence of palladium(II)/Cul In Et3N at room temperature to give E-enynes In good yields. The methodology represents a general and efficient protocol for carrying out the synthesis of E-enynes under mild conditions with complete retention of configuration.

Catalytic asymmetric synthesis of 1,3-enyne scaffolds: Design and synthesis of conjugated nitro dienynes as novel Michael acceptors and development of a new synthetic methodology

A novel catalytic enantioselective synthesis of functionalized 1,3-enynes has been developed featuring the design and synthesis of conjugated nitro dienynes as a useful new class of Michael acceptors. Moreover, a simple, yet flexible catalytic cascade approach to functionalized enantioenriched acyclic α,β-enones and cyclic dienones has also been developed.

Efficient synthesis of enynes by tetraphosphine-palladium-catalysed reaction of vinyl bromides with terminal alkynes

Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as catalyst, a range of vinyl bromides undergoes Sonogashira cross-coupling reaction with a variety of alkynes, leading to

Stereoselective synthesis of enynes by nickel-catalyzed cross-coupling of divinylic chalcogenides with alkynes

(Z,Z)- and (E,E)-divinylic selenides and telurides undergo direct coupling with terminal alkynes in the presence of a nickel/CuI catalyst at room temperature to give (Z)- and (E)-enyne systems in good yields and with complete retention of configuration.

Synthesis of alkylidenecyclopentenones and dialkylidenecyclopentenones via the coupling of propargylic alcohol and 2-alkyne-1,4-diol derivatives with cyclopropylcarbene-chromium complexes

The coupling of propargylic alcohols and their derivatives with cyclopropylcarbene-chromium complexes has been investigated. The coupling reaction leads to alkylidenecyclopentenones or alkoxyalkyl-cyclopentenones, depending on the leaving group ability of

Synthesis of Aryl- and Vinylacetylene Derivatives by Copper-Catalyzed Reaction of Aryl and Vinyl Iodides with Terminal Alkynes

The coupling reaction of aryl iodides with terminal alkynes by using a catalyst system of CuI-PPh3 in the presence of K2CO3 as base gives the corresponding arylated alkynes in excellent yields.Addition of PPh3 is essential for the reaction to proceed catalytically.Vinyl iodides also react smoothly with the alkynes to give enyne compounds with retention of the configurations.While DMF and DMSO can be used as solvents, DMSO is found to be effective for the reaction with aliphatic terminal alkynes.A reaction mechanism involving initial formation of copper acetylide species coordinated by PPh3 followed by reaction of aryl and vinyl iodides is proposed.

Cross-Coupling of Organosilanes with Organic Halides Mediated by Palladium Catalyst and Tris(diethylamino)sulfonium Difluorotrimethylsilicate

In the presence of tris(diethylamino)sulfonium difluorotrimethylsilicate (TASF) and allylpalladium chloride dimer as a catalyst, organosilicon compounds like vinyl-, ethynyl-, and allylsilanes react with such organic halides as aryl, vinyl, and allyl halides to give the corresponding coupled products in synthetically useful yields in a stereospecific and chemoselective manner.

Palladium-Catalyzed Propargylic vs. Allylic Alkylation

The relative reactivities of allylic propargylic acetates toward palladium(0)-catalyzed substitution by various nucleophiles were studied bu using three types of model substrates: (a) monofunctional allylic and propargylic acetates with similar structural properties; (b) a bifunctional substrate containing both allyl and propargyl functionalities with no apparent interaction between them; (c) conjugated bifunctional systems, in which the two functionalities may interact with one another.Palladium(0)-catalyzed substitution of propargylic acetates by various carbon nucleophiles was found to be less general than the analogous substitution of allylic acetates.Three modes of reactivity were observed, corresponding to three groups of nucleophiles; (a) stabilized carboanions such as sodium dimethyl malonate, which do not react with propargylic acetates but react readily with allylic acetates; (b) nonstabilized organometallics such as phenylzinc chloride, which react with propargylic and allylic acetates at comparable rates (reaction with the former yielding the allenic product exlusively); and (c) allyl- and allenylstannanes, which react with allylic acetates but do not react with isolated propargylic acetates (except for special cases where the propargylic acetate is also an allylic one).Certain similarities between regioselectivity phenomena in organopalladium and organocopper chemistry are discussed.