72735-70-7

Upstream product

• 106-38-7 para-bromotoluene 
• 15727-65-8 1-ethynylnaphthalene 
• 624-31-7 4-tolyl iodide 
• 1139705-28-4 naphthalene-1-yl 1H-imidazole-1-sulfonate 
• 766-97-2 4-n-methylphenylacetylene 
• 5720-05-8 4-methylphenylboronic acid 
• 77295-63-7 1-(2,2-dibromovinyl)naphthalene 
• 86-55-5 1-naphthalenecarboxylic acid 
• 321-38-0 1-Fluoronaphthalene 
• 68211-49-4 1-naphthyl tosylate 
• 90-11-9 1-Bromonaphthalene 
• 90-14-2 1-Iodonaphthalene 

Downstream Products

• 1236115-71-1 methyl 2-(1-acetyl-4-(1-naphthyl)-5-(4-methylphenyl)-1H-pyrrol-2-yl)ethanoate 
• 1236115-70-0 methyl 2-(1-acetyl-4-(4-methylphenyl)-5-(1-naphthyl)-1H-pyrrol-2-yl)ethanoate 
• 36288-25-2 (Z)-1-(4-methylphenyl)-2-(naphth-1-yl)ethene 
• 52823-29-7 2-(4'methylphenyl)naphtho<2,1-b>thiophene 

Relevant academic research and scientific papers

Palladium-catalyzed decarbonylative sonogashira coupling of terminal alkynes with carboxylic acids

A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxylic acids including those bioactive ones could couple readily with various terminal alkynes, thus providing a relative general method for preparing internal alkynes.

LiHMDS-Promoted Palladium-Catalyzed Sonogashira Cross-Coupling of Aryl Fluorides with Terminal Alkynes

A highly efficient Pd-catalyzed Sonogashira coupling of various aryl fluorides with terminal alkynes in the presence of LiHMDS was developed. Both unreactive electron-rich fluoroarenes and electron-poor fluoroarenes proceeded smoothly and afforded the cor

Synthesis, Characterization, and Functionalization of 1-Boraphenalenes

1-Boraphenalenes have been synthesized by reaction of BBr3 with 1-(aryl-ethynyl)naphthalenes, 1-ethynylnaphthalene, and 1-(pent-1-yn-1-yl)naphthalene and they can be selectively functionalized at boron or carbon to form bench-stable products. A

Three Different Reactions, One Catalyst: A Cu(I) PNP Pincer Complex as Catalyst for C-C and C-N Cross-Couplings

An air-stable, thermally robust, and well-defined Cu(I) PNP pincer complex based on the 2,6-diaminopyridine scaffold is described. This complex is an active catalyst for the cross-couplings of a range of aryl and heteroaryl (including benzoxazole, thiazole, pyridine, and thiophene) halides with different organomagnesium reagents, alkynes, and aryl-amines giving excellent to good isolated yields.

Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur

A simple yet effective method for the formation of thiophene-fused π-systems is reported. When arylethynyl-substituted polycyclic arenes were heated in DMF in the presence of elemental sulfur, the corresponding thiophene-fused polycyclic arenes were obtained via cleavage of the ortho-C-H bond. Thus, arylethynylated naphthalenes, fluoranthenes, pyrenes, corannulenes, chrysenes, and benzo[c]naphtho[2,1-p]chrysenes were effectively converted into the corresponding thiophene-fused π-systems. Apart from polycyclic hydrocarbons, thiophene derivatives are also susceptible to this reaction. The practical utility of this reaction is demonstrated by preparations on the decagram scale, one-pot two-step reaction sequences, and multiple thiophene annulations.

Cross-coupling reactions catalyzed by an N-heterocyclic carbene-Pd(ii) complex under aerobic and CuI-free conditions

A Pd-complex, (Cat. 3), has been successfully employed as a highly efficient and recyclable catalyst for the Sonogashira and Heck reactions of aryl bromides with various terminal acetylenes and olefins. The catalytic reactions proceed with excellent yields with a low catalyst loading (1.0 mol%) under aerobic and CuI-free conditions. A plausible mechanism has also been proposed for the reaction. the Partner Organisations 2014.

Copper-catalyzed synthesis of internal alkynes via domino coupling between 1,1-dihalo-1-alkenes and arylboronic acids

We have developed the practical copper-catalyzed formation of various internal alkynes via domino couplings between 1,1-dihalo-1-alkenes and arylboronic acids in the presence of low-cost 8-hydroxylquinoline as the ligand.

Microwave-promoted copper-free Sonogashira-Hagihara couplings of aryl imidazolylsulfonates in water

Aryl imidazol-1-ylsulfonates have been efficiently cross-coupled with aryl-, alkyl-, and silylacetylenes in neat water under copper-free conditions at 110 °C assisted by microwave irradiation. Using 0.5mol% of an oxime palladacycle as precatalyst, 2-dicyclohexylphosphino-2′,6′- dimethoxybiphenyl (SPhos, 2mol%) as ligand, hexadecyltrimethylammonium bromide (CTAB) as additive, and triethylamine (TEA) as base, a wide array of disubstituted alkynes has been prepared in good to high yields in only 30min. Copyright

Silver triflate-catalyzed cyclopropenation of internal alkynes with donor-/acceptor-substituted diazo compounds

Silver triflate was found to be an efficient catalyst for the cyclopropenation of internal alkynes using donor-/acceptor-substituted diazo compounds as carbenoid precursors. Highly substituted cyclopropenes, which cannot be synthesized directly via rhodium(II)-catalyzed carbenoid chemistry, can now be readily accessed.

An efficient copper(I) complex catalyzed Sonogashira type cross-coupling of aryl halides with terminal alkynes

A wide range of arylated alkynes are synthesized from the corresponding aryl halides and terminal alkynes through Sonogashira type cross-coupling reactions through C(aryl)-C bond formation in the presence of a catalytic amount of N,N′-dibenzyl BINAM-CuI complex under mild reaction conditions.