58040-58-7

Upstream product

• 5876-69-7 2,4-diphenylbut-3-yn-2-ol 
• 98-85-1 1-Phenylethanol 
• 29578-46-9 trimethyl(3-phenylprop-2-yn-1-yl)silane 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 14856-75-8 1-phenyl-1-trimethylsilyloxyethane 
• 536-74-3 phenylacetylene 
• 93321-44-9 1,3-diphenylprop-2-yn-1-yl acetate 
• 75-24-1 trimethylaluminum 
• 5075-59-2 diethyl(phenylethynyl)aluminum 
• 585-71-7 (1-bromoethyl)benzne 
• 100-58-3 phenylmagnesium bromide 
• 100-42-5 styrene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 73922-81-3 4-phenyl-but-3-yn-2-ol 

Downstream Products

• 53544-89-1 1,1'-(1-methyl-1,2-propadiene-1,3-diyl)bisbenzene 
• 56516-64-4 penta-2,3-diene-2,4-diyldibenzene 

Relevant academic research and scientific papers

Somophilic alkynylation of unreactive alkenes enabled by iron-catalyzed hydrogen atom transfer

We report an efficient and practical iron-catalyzed hydrogen atom transfer protocol for assembling acetylenic motifs into functional alkenes. Diversities of internal alkynes could be obtained from readily available alkenes and acetylenic sulfones with exc

Cu-Photoredox-catalyzed C(sp)-C(sp3) coupling of redox-active esters with terminal alkynes

Visible-light-induced C(sp)-C(sp3) coupling of redox-active esters with terminal alkynes has been developed. The activation of carboxylic acids as their redox-active ester derivatives was important for this decarboxylative alkynylation. The strategy established here facilitates the straightforward introduction of triple-bonded functional groups and avoids additional photocatalysts. A wide range of primary, secondary and tertiary acids can be converted into the target products; so this reaction exhibits a broad substrate scope and tolerance of functional groups. Mechanistic experiments suggested that this reaction may undergo a radical process. Under mild reaction conditions, a copper acetylide ligand as a photocatalyst delivered an electron to redox-active ester derivatives, and generated alkyl radicals. The radicals reacted with Cu(ii) to deliver a Cu(iii) complex, and then reductive elimination gave the products.

A Copper-Catalyzed Sonogashira Coupling Reaction of Diverse Activated Alkyl Halides with Terminal Alkynes Under Ambient Conditions

We describe a copper-catalyzed Sonogashira coupling reaction of alkyl halides with terminal alkynes under ambient conditions, efficiently providing a versatile tool for the construction of substituted alkynes. A new proline-based N,N,P-ligand is utilized to promote the transformation under a mild reaction condition. Diverse alkyl halides, such as primary and secondary (hetero)benzyl chlorides and bromides, secondary and tertiary α-bromo amides and propargylic bromide, are applicable to provide a wide array of alkynes. (Figure presented.).

Regioselective Iron-Catalysed Cross-Coupling Reaction of Aryl Propargylic Bromides and Aryl Grignard Reagents

An iron-catalysed Kumada-type cross-coupling reaction between aryl substituted propargylic bromides and arylmagnesium reagents has been developed. Propargylic coupling products were the main or only outcome, and propargyl/allene regioselectivity was shown to depend on the electronic nature of the substituents on the triple bond of the substrate and on the arylmagnesium halide. Best selectivities were observed when electron donating substituents were present in either reagent. The process is stereoespecific, occurs with configuration inversion and no carbon-based radicals seem to be involved in the mechanism. (Figure presented.).

Palladium-catalyzed, ligand-free SN2’ substitution reactions of organoaluminum with propargyl acetates for the synthesis of multi-substituted allenes

We describe a convenient method for the synthesis of multi-substituted allenes from SN2′ substitution reactions organoaluminum with propargyl acetates: The SN2′ substitution reaction of organoaluminum (0.4 mmol) with propargyl acetat

Application of Hantzsch Ester and Meyer Nitrile in Radical Alkynylation Reactions

The first example of constructing a Csp3-Csp bond with substituted Hantzsch ester and Meyer nitrile is reported. When benziodoxole-activated alkyne was applied as the alkynyl donor, products containing Csp3-Csp bonds involving primary, secondary, and tertiary carbon centers were achieved in up to 97% yields. K2S2O8 was the optimum radical initiator in this reaction.

Synthesis of multi-substituted allenes from organoalane reagents and propargyl esters by using a nickel catalyst

A highly efficient and simple route for the synthesis of multi-substituted allenes has been developed by a nickel catalyzed SN2′ substitution reaction of propargyl esters with organic aluminium reagents under mild conditions, which gave the corresponding multi-substituted allenes in good to excellent yields (up to 92%) and high selectivities (up to 99%) at 60 °C for 6 h in THF. Aryls bearing electron-donating or electron-withdrawing groups in propargyl esters gave products in good yields. In addition, the multi-substituted allenes bearing a thienyl or a pyridyl group were obtained in 95-97% selectivities with isolated yields of 72-83%. Furthermore, the SN2′ substitution reaction worked efficiently with propargyl carbonate compounds as well. On the basis of the experimental results, a possible catalytic cycle has been proposed.

Highly Efficient Synthesis of Multi-Substituted Allenes from Propargyl Acetates and Organoaluminum Reagents Mediated by Palladium

A simple and mild catalytic S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents is reported. The S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents mediated by Pd(PhP 3) 2 Cl 2 (1 mol%)/PPh 3 (2 mol%)/K 2 CO 3 in tetrahydrofuran at 60 °C for 3-4 hours afforded the corresponding multi-substituted allenes in good yields (up to 94%) with high selectivities (up to 99%). The process was simple and easily performed, which offers an efficient method to synthesize the multi-substituted allene derivatives.

Transmetalation of Alkylzirconocenes in Copper-Catalyzed Alkyl–Alkynyl Cross-Coupling Reactions

A simple copper-catalyzed alkyl–alkynyl cross-coupling strategy has been developed using the reaction between alkynyl bromides and alkylzirconocenes. The alkylzirconocenes were generated in situ via regioselective addition of Schwartz's reagent (ZrCp2HCl) on to alkenes. The reaction has a broad scope, a range of functionalized bromoalkynes and alkylzirconium reagents were successfully coupled, resulting in moderate to good yields of the desired internal alkynes. (Figure presented.).

Regio- and Stereospecific Copper-Catalyzed Substitution Reaction of Propargylic Ammonium Salts with Aryl Grignard Reagents

We have developed a copper-catalyzed substitution reaction of propargylic ammonium salts with aryl Grignard reagents. The reaction is stereospecific and α-regioselective and proceeds with exceptional functional group tolerance. Conveniently, a stable, inexpensive, and commercially available copper salt is used and no added ligand is required.