24765-03-5

Upstream product

• 536-74-3 phenylacetylene 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 4392-24-9 Cinnamyl bromide 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 3757-88-8 tributylstannylethynylbenzene 
• 21040-45-9 Cinnamyl acetate 
• 637-44-5 phenylpropyolic acid 
• 124-38-9 carbon dioxide 
• 103-54-8 cinnamyl acetate 
• 300-57-2 allylbenzene 
• 13984-49-1 (phenylethynyl)zinc chloride 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 63124-66-3 (1E)-1,5-diphenylpent-1-en-4-yn-3-ol 

Downstream Products

• 31552-02-0 (E)-penta-1,2,4-triene-1,5-diyldibenzene 
• 93875-18-4 2,6-diphenylcyclohex-2-enone 
• 105480-02-2 1,2,4,5-tetrabromo-1,5-diphenylpent-1-ene 

Relevant academic research and scientific papers

Synthesis of 1,4-enynes: Via nickel-catalyzed cross-coupling of allylic alcohols with alkynylzinc reagents

Synthesis of 1,4-enynes was performed via nickel-catalyzed cross-coupling of allylic alcohols with alkynylzinc reagents. The reaction features high regio- and E/Z-selectivity when aryl-substituted allylic alcohols were employed. The method also exhibits a wide scope of substrates and good compatibility of functional groups. This journal is

Preparation method of 1, 4 enyne compound

The invention discloses a preparation method of a 1, 4 enyne compound, which comprises the following steps of in an inert gas atmosphere, adding allyl alcohol, acetylenic acid and a combined catalyst into an organic solvent, and stirring and reacting for 12-24 hours at the temperature of 80-100 DEG C to obtain a reaction solution, wherein the combined catalyst is prepared from organic palladium, villiaumite and cesium fluoride, and the villiaumite is bis (trifluoromethanesulfonimide) salt or bis (trifluoromethanesulfonate), and extracting the reaction solution by using water and ethyl acetate to remove part of the reaction solvent, drying and concentrating an organic phase, and purifying by using a petroleum ether/ethyl acetate developing solvent system through thin layer chromatography to obtain the 1, 4-eneyne compound. The preparation method is simple and convenient to operate, the obtained by-products only comprise water and carbon dioxide, and the method has the advantages of being high in atom economy and environmentally friendly; in addition, the preparation method is low in raw material price and wide in applicable substrate range.

Regioselective and Redox-Neutral Cp*IrIII-Catalyzed Allylic C?H Alkynylation

Herein, we report a Cp*IrIII-catalyzed highly regioselective and redox-neutral protocol for the construction of 1,4-enynes from unactivated olefins and bromoalkynes via intermolecular allylic C?H alkynylation. The developed mild reaction conditions tolerate a broad range of common functional groups, even enabling selective alkynylation of allylic C?H bonds in the presence of other prominent directing groups. Mechanistic experiments including the isolation of a catalytically active IrIII-allyl species support an intermolecular allylic C?H activation followed by an electrophilic alkynylation.

Copper-Catalyzed Allylic C?H Alkynylation by Cross-Dehydrogenative Coupling

C?H bond functionalization is a well-developed concept that has been thoroughly studied and gives entry to rather complex molecules without the need for previous derivatization of the substrates. The use of copper complexes in allylic C?H bond functionalization under oxidative conditions as an alternative to the well-established palladium-based methodologies remains largely underdeveloped. Here, we show for the first time a selective cross-dehydrogenative coupling reaction between underivatized allylic substrates and terminal alkynes to produce 1,4-enynes in high yields in a single step, using an in situ synthesized copper catalyst and an oxidant.

Palladium(II)-Catalyzed Deacylative Allylic C-H Alkylation

The first deacylative allylic C-H alkylation has been established by employing the palladium-catalyzed allylic C-H activation and decarboxylative nucleophile generation. A wide scope of nucleophiles are tolerated and densely functionalized alkylation products turn out to be furnished in moderate to good yield. More importantly, this strategy provides an alternative method for the allylic C-H alkylation with less stabilized carbon nucleophiles, and can be further expanded to the synthesis of unconjugated enynes.

One-Pot Synthesis of Decahydropyrene via Tandem C-H Activation/Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition

A novel decahydropyrene synthesis has been successfully developed involving a tandem rhodium-catalyzed C-H activation/intramolecular Diels-Alder reaction/1,3-dipolar cycloaddition cascade process by using diazole as a traceless directing group. The advantage of this one-pot strategy is a quite simple, efficient, highly stereoselective, and unique product structure.

Chemo- and regioselective reductive deoxygenation of 1-en-4-yn-ols into 1,4-enynes through FeF3 and TfOH co-catalysis

We report chemo- and regioselective direct reductive deoxygenation of 1-en-4-yn-3-ols into 1,4-enynes through FeF3 and TfOH cooperative catalysis under NBSH-mediated conditions. Further, we show the efficient synthesis of a pharmaceutically significant 1,4-enyne. The present methodology can also be used for chemo- and regioselective direct deoxygenation of other alcohols.

Decarboxylative/Sonogashira-type cross-coupling using PdCl2(Cy?Phine)2

The PdCl2(Cy?Phine)2 precatalyst containing the meta-terarylphosphine ligand, Cy?Phine, can effectively mediate decarboxylative cross-coupling with a diverse range of (hetero-)aryl, aryl and alkyl chlorides including those with unprotected functionality. Using a facile and robust protocol, this process was extended to the first synthesis of symmetrical di(heteroaryl)alkynes via tandem Sonogashira/decarboxylative cross-coupling of heteroaryl chlorides and propiolic acid.

Synthesis of Multinuclear Copper Complexes Bridged by Diquinolylamidinates and Their Application to Copper-Catalyzed Coupling of Terminal Alkynes and Aryl, Allyl, and Benzyl Halides

A dinuclear copper complex containing N,N′-diquinolylformamidinate and a tetranuclear copper complex containing N,N′-diquinolylacetamidinate were synthesized. The structure of complexes was confirmed by X-ray analysis, showing that copper atoms were bridg

A Pd(0)-catalyzed direct dehydrative coupling of terminal alkynes with allylic alcohols to access 1,4-enynes

A direct dehydrative coupling of terminal alkynes with allylic alcohols catalyzed by Pd(PPh3)4 with an N,P-ligand assisted by Ti(OiPr)4 has been developed. The coupling reaction tolerates various functional groups, providing a valuable synthetic tool to access 1,4-enynes.