111468-65-6

Upstream product

• 628-71-7 1-Heptyne 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 693-02-7 hex-1-yne 
• 100-59-4 phenylmagnesium chloride 
• 77973-37-6 (E)-1-chloro-non-1-en-3-yne 
• 67502-64-1 bis-(E)-β-styryl selenide 
• 103-64-0 bromostyrene 
• 371250-28-1 (E)-1-iodo-1-(tributylstannyl)-2-phenylethene 
• 28557-00-8 phenylzinc chloride 
• 15719-56-9 1-heptynyltrimethylsilane 

Downstream Products

• 1174643-34-5 (1E,3Z-4-ethyl-nona-1,3-dienyl)benzene 

Relevant academic research and scientific papers

Versatile palladium(II)-catalyzed Negishi coupling reactions with functionalized conjugated alkenyl chlorides

Under palladium catalysis, we found that organozincate reagents, generated in situ, by reaction of Grignard compounds with less than molar amounts of zinc chloride, in the presence of conjugated alkenyl chlorides, give rapidly and cleanly the corresponding coupling product in high yields. In this way, aryl as well as primary and secondary alkyl substituents have been introduced successfully. The selectivity of the reaction allows to prepare various functionalized conjugated enynes and dienes from chloroenyne and chlorodiene derivatives bearing a functional group.

An efficient synthesis of stereodefined enynes and dienes via Pd-catalyzed reaction of chloroenynes and chlorodienes with Grignard reagents

In the presence of PdCl2(PPh3)2 and Et3N, chloroenynes and chlorodienes react rapidly under mild conditions with various Grignard reagents to give isomerically pure conjugated enynes, dienes, dienynes and triene

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

Synthesis of (Z)-tributylstannyl enynes: Systematic studies of Sonogashira cross-coupling reactions between (E)-1-iodovinyl-1-tributylstannanes and terminal acetylenes using amines or tetrabutylammonium hydroxide (TBAOH) as activator

Sonogashira cross-coupling reactions involving (E)-iodo vinyl stannanes and terminal acetylenes were carried out in the presence of Pd(PPh 3)4, CuI and several amines, affording (Z)-tributylstannyl enynes in moderate to good yields (

CuI-catalyzed Suzuki-Miyaura and Sonogashira cross-coupling reactions using DABCO as ligand

In the presence of TBAB, CuI-catalyzed Suzuki-Miyaura cross-coupling of vinyl halides and aryl halides with arylboronic acids was conducted smoothly to afford the corresponding diarylethenes and polyaryls in moderate to good yields using DABCO (1,4-diazabicyclo[2.2.2]octane) as the ligand. We also found that the inexpensive CuI/DABCO catalytic system was effective for Sonogashira cross-couplings of aryl halides and vinyl halides. A variety of aryl halides and vinyl halides including activated aryl chlorides underwent the coupling with terminal alkynes in moderate to excellent yields.

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.

Stereoselective manganese-catalyzed coupling reaction of conjugated chloroenynes and chlorodienes with Grignard reagents

In the presence of the soluble complex MnCl2?2LiCl (3%), conjugated chloroenynes and chlorodienes readily react with alkyl Grignard reagents in THF-DMPU to afford stereoselectively enynes and dienes in good to excellent isolated yields.

Substituted 4-(alk-2-ynylsulfinyl)morpholines: preparation and conversion into substituted allenes by hydrolytic desulfinylation

4-(Alka-1,2-dienylsulfinyl)morpholines 1 were converted into the title compounds 2 by γ-deprotonation with methyllithium via a complex-induced proximity effect (CIPE) process, followed by reaction with electrophiles.Compounds 2 were hydrolysed or deuterol

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.

Copper-catalyzed coupling reaction of aryl and vinyl halides with terminal alkynes

Coupling reaction of aryl and vinyl halides with terminal alkynes using a catalyst system of copper (I) iodide - triphenylphosphine proceeds efficiently in the presence of potassium carbonate to give the corresponding unsymmetrical acetylenes in good yield.