14491-41-9

Upstream product

• 106-39-8 bromochlorobenzene 
• 628-71-7 1-Heptyne 
• 106-46-7 para-dichlorobenzene 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 19821-84-2 1-bromohept-1-yne 
• 637-87-6 1-Chloro-4-iodobenzene 
• 5663-96-7 oct-2-ynoic acid 
• 693-02-7 hex-1-yne 

Relevant academic research and scientific papers

Synthesis of trisubstituted olefins via nickel-catalyzed decarboxylative hydroalkylation of internal alkynes

A novel NiH-catalyzed decarboxylative hydroalkylation of internal alkynes has been developed. Trisubstituted olefins were obtained in moderate to good yields with good regioselectivities. The reaction involves cis addition of NiH to the internal alkyne. The reaction shows good functional-group tolerance.

Copper-catalyzed decarboxylative coupling of aryl halides with alkynyl carboxylic acids performed in water

Most alkynes are volatile liquids, which are relatively difficult to use and to transport. In contrast, alkynyl carboxylic acids offer a stable and attractive alternative for the alkynylation reactions. Here, we employed alkynyl carboxylic acids as reaction partners for the alkynylation of aryl halides. Copper-catalyzed decarboxylative coupling, including various challenging aryl bromides with phenylpropiolic acid, was performed in water without using co-solvents with good yields. Our approach provides a low-loading, low-cost, stable and environmentally friendly copper catalyst system for decarboxylative coupling.

Synthesis of diarylalkynes by iron/copper co-catalyzed decarboxylative sp-sp2 coupling of alkynyl carboxylic acids and aryl halides

The highly effective decarboxylative sp-sp2 coupling of alkynylcarboxylic acids with various aryl halides was carried in the presence of low-cost and readily available copper(I) iodide/iron(III) acetylacetonate under ligand-free and palladium-free conditions using low catalyst loadings. This protocol makes such coupling reactions more practical and useful. Copyright

Copper-catalyzed cross-coupling of alkyl and aryl grignard reagents with alkynyl halides

(Chemical Equation Presented) Good old copperl A new general procedure to couple aliphatic and aromatic Grignard reagents with alkynyl halides under copper catalysis is described (see scheme; NMP=N-methylpyrrolidinone). The reaction is chemoselective and allows preparation of a vast array of simple and functionalized internal alkynes in high yields.

Copper-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with aryl halides

The copper-catalyzed decarboxylative reactions of alkynyl carboxylic acids with aryl halides were performed under relatively mild reaction conditions. Benzofurans could be further prepared smoothly by a one-pot domino protocol on the basis of decarboxylative cross-coupling of 2-iodophenol.

Efficient copper-free PdCl2(PCy3)2- catalyzed sonogashira coupling of aryl chlorides with terminal alkynes

Under copper-free conditions and with Cs2CO3 as a base, PdCl2(PCy3)2 showed high catalytic activity for cross-coupling of electron-rich, elctron-neutral, and electron-deficient aryl chlorides with a variety of terminal alkynes in DMSO at 100-120 °C affording internal arylated alkynes in good to excellent yields.

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.

Rates and Regioselectivities of the Palladium-Catalyzed Ethynylation of Substituted Bromo- and Dibromobenzenes

The Pd(0)/Cu2Br2-catalyzed ethynylation of 1,2-dibromo-4-nitro- and 1,2-dibromo-3-nitrobenzenes provide rapidly the product in which the bromine para or ortho to the nitro group is displaced, whereas the corresponding dibromoacetamidobenzenes provide the product of meta displacement slowly.Investigation of the rates of a series of para-substituted bromobenzenes indicates that the reaction is zero-order with respect to the heptyne and bromobenzene concentration, with a Hammett ρ value of 2.8.