3287-02-3

Usage

InChI:InChI=1/C15H12/c1-13-7-9-15(10-8-13)12-11-14-5-3-2-4-6-14/h2-10H,1H3

Upstream product

• 15726-08-6 1,1-dichloro-2-phenyl-2-p-tolyl-ethene 
• 13146-23-1 copper(I) phenylacetylenide 
• 624-31-7 4-tolyl iodide 
• 615-37-2 ortho-methylphenyl iodide 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 106-38-7 para-bromotoluene 
• 17024-97-4 (α,α-Dichlor-benzyl)-(4-methyl-benzyl)-sulfon 
• 65614-77-9 C₁₅H₁₆N₄ 
• 7664-41-7 ammonia 
• 114812-70-3 C₃₇H₃₁Sb 
• 1038-95-5 Tri(p-tolyl)phosphine 
• 5395-43-7 tri(p-tolyl)antimony 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 

Downstream Products

• 24792-68-5 trans-1-Phenyl-2-(4'-phenyl-stilben-4-yl)-acetylen 
• 23798-54-1 trans-1-Phenyl-2-(4-(2-naphthyl-⁽¹⁾-ethenyl)-phenyl)-acetylen 
• 23798-53-0 trans-1-Phenyl-2-(4-(2-naphthyl-⁽²⁾-ethenyl)-phenyl)-acetylen 
• 23798-51-8 trans-1-Phenyl-2-(3',4',5'-trimethoxy-stilben-4-yl)-acetylen 
• 23798-50-7 trans-1-Phenyl-2-<3',4'-dimethoxy-stilben-4-yl>-acetylen 
• 23798-52-9 trans-1-Phenyl-2-<4'-phenoxy-stilben-4-yl>-acetylen 
• 53348-77-9 trans,trans-p-Phenylethinyl-p'-styrylstilben 
• 57341-98-7 4-(phenylethynyl)benzaldehyde 
• 2431-00-7 p-methylbenzil 
• 23798-55-2 3-[(E)-2-(4-Phenylethynyl-phenyl)-vinyl]-pyridine 
• 142438-06-0 3-cyano-2,3-diphenyl-1-tolylcyclopropene 
• 131202-79-4 1-Methyl-2-phenyl-3-p-tolyl-1H-1-aza-phenalene 
• 131202-88-5 1-Methyl-3-phenyl-2-p-tolyl-1H-1-aza-phenalene 
• 784-75-8 2-(p-tolyl)-2,3-dihydro-1H-inden-1-one 

Relevant academic research and scientific papers

Syntheses, characterization, and structural studies of copper(I) complexes containing 1,1′-bis(di-tert-butylphosphino)ferrocene (dtbpf) and their application in palladium-catalyzed Sonogashira coupling of aryl halides

Four copper(i) complexes [Cu4(μ3-Cl) 4(μ-dtbpf)2] (1), [Cu6(μ3-Br) 4(μ2-Br)2(μ-dtbpf)3] (2), [Cu4(μ2-I)2(μ3-I) 2(μ-dtbpf)2] (3) and [Cu2(μ1- CN)2(κ2-dtbpf)2] (4) were prepared using CuX (X = Cl, Br, I, CN) and 1,1′-bis(di-tert-butylphosphino)ferrocene (dtbpf) in 2:1 molar ratio in DCM-MeOH (50:50 V/V) at room temperature. These complexes were characterized by elemental analyses, IR, 1H and 31P NMR, ESI+-MS and electronic absorption spectroscopy. Molecular structures of the complexes 1, 2 and 3 were determined crystallographically. Complexes 1 and 3 are tetrameric Cu(i) pseudo-cubane like structures with a Cu4Cl4 core, and a stepped cubane-like structure with a Cu4I4 core, respectively, whereas complex 2 shows a trimeric copper(i) framework containing two [Cu3(μ 3-Br)2(μ2-Br)] units that are bridged by three bidentate μ-dtbpf ligands. Each [Cu3(μ3-Br) 2(μ2-Br)] unit forms a pyramid with one copper atom at the apex and one of the triangular faces capped by one bromine atom. All the complexes were found to be efficient catalysts for the Sonogashira reaction. The coupling products were obtained in moderate to good yields (58-99%) using Pd loadings of 0.2 mol% as well as complex loading of 0.1 mol%. The 31P NMR studies show that all the complexes are unstable during the course of tandem catalytic reaction and the dtbpf ligand migrates from copper(I) to palladium(II), which promotes palladium Sonogashira cross-coupling of activated and non-activated aryl halides. the Partner Organisations 2014.

Palladium catalyzed multicomponent reactions in ordered sequence: New syntheses of o,o′-dialkylsubstituted diarylacetylenes and diarylalkylidenehexahydromethanofluorenes

Catalytic one-pot reactions of aromatic iodides with alkyl halides, phenylacetylene or diphenylacetylene, potassium acetate or carbonate, norbornene and palladium acetate in DMF or DMA are reported. A high selectivity towards dialkylsubstituted diarylacetylenes and diarylalkylidenehexahydromethanofluorenes, respectively, has been reached.

A Ni(OAc)2·4H2O-catalysed Sonogashira-type coupling reaction of aryl iodides and terminal alkynes in the presence of CuI

An effective and promising Ni/Cu catalytic system for the coupling of aryl iodides with various terminal alkynes has been developed. For the first time the readily available chiral amino alcohol has been employed as the ligand for the Pd-free Sonogashira

Copper-free, efficient, palladium (II)-catalyzed coupling of unactivated aryl iodides with terminal alkynes

Palladium(II)-catalyzed coupling of terminal alkynes with unactivated aryl iodides occurs at room temperature in good to excellent yields in the presence of tetrabutylammounium bromide as additive and piperidine as base in a tetrahydrofuran-water solution

SYNTHESIS AND REDUCTIVE ELIMINATION OF TRIARYLBIS(PHENYLETHYNYL)ANTIMONY (V)

Triarylbis(phenylethynyl)antimony (V) (1a-1c) were synthesized from triarylantimony dibromide and lithium phenylacetylide.Thermolytic reductive elimination of 1a-1c took place at 110 deg C and the aryl-alkynyl coupling product (3) increased as the aryl group became more electronegative.The result is consistent with the apical-apical coupling from the trigonal bipyramidal structures, which was predicted to be symmetry-allowed by Hoffmann.

A thiocyanato-bridged copper(i) cubane complex and its application in palladium-catalyzed Sonogashira coupling of aryl halides

Reaction of copper(i) thiocyanate with 1,1′-bis(di-tert- butylphosphino) ferrocene (dtbpf) in a 2:1 molar ratio in DCM-MeOH (50:50 V/V) afforded a tetranuclear copper(i) complex [Cu4(μ3-SCN) 4(κ1-P,P-dtbpf)

The nickel-catalyzed Sonogashira-Hagihara reaction

The Sonogashira-Hagihara coupling of terminal acetylenes with aryl iodides in the presence of a nickel catalyst and CuI was investigated. The reaction proceeds rapidly in aqueous dioxane in the presence of Ni(PPh3)2Cl2 wit

Palladium-catalyzed reaction of a sterically constrained trialkyne: A dimerization-type reaction with a surprising finale

The intramolecular reaction of a triyne promoted by palladium results in the formation of an enyne and coupling of the third alkyne with the phosphine. (C) 2000 Elsevier Science Ltd.

Pd nanoparticles catalyst supported on TMU-16-NH2 metal-organic framework for Sonogashira cross-coupling reaction

The current article presented the synthesis and characterization of a novel, unique, and effective heterogeneous catalytic system, based on a metal-organic framework named Pd@TMU-16-NH2 with high catalytic performance. Also, the application of

Introduction of a Recyclable Basic Ionic Solvent with Bis-(NHC) Ligand Property and The Possibility of Immobilization on Magnetite for Ligand- and Base-Free Pd-Catalyzed Heck, Suzuki and Sonogashira Cross-Coupling Reactions in Water

A new versatile and recyclable NHC ligand precursor has been developed with ligand, base, and solvent functionalities for the efficient Pd-catalyzed Heck, Suzuki and Sonogashira cross-coupling reactions under mild conditions. Furthermore, NHC ligand precursor was immobilized on magnetite and its catalytic activity was also evaluated towards the coupling reactions as a heterogeneous catalyst. The NHC ligand precursor was prepared with imidazolium functionalization of TCT followed by a simple ion exchange by hydroxide ions. However, the results revealed an excellent catalytic activity for the both homogeneous and heterogeneous catalytic systems. 1.52?g.cm?3 and 1194 cP was obtained for the density and viscosity of the NHC ligand precursor respectively. On the other hand, the heterogeneous type could be readily recovered from the reaction mixture and reused for several times while preserving its properties. Heterogeneous nature of the magnetic catalyst was studied by hot filtration, mercury poisoning, and three-phase tests. High to excellent yields were obtained for all entries for the both homogeneous and heterogeneous catalysts, which reflects the high consistency of the catalyst. Graphic Abstract: [Figure not available: see fulltext.]