4044-57-9

Upstream product

• 13146-23-1 copper(I) phenylacetylenide 
• 90-14-2 1-Iodonaphthalene 
• 90-11-9 1-Bromonaphthalene 
• 6928-78-5 Bis(phenylethynyl)magnesium 
• 3757-88-8 tributylstannylethynylbenzene 
• 99747-74-7 1-naphthyl triflate 
• 85924-94-3 1-Benzylidene-1H-cyclobutanaphthalene 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 4440-01-1 lithium phenylacetylide 
• 4706-43-8 1-benzyl-1H-benzotriazole 
• 890-50-6 [1]naphthylmethylen-aniline 
• 78569-38-7 (E)-1-(naphthalen-1-yl)-N-phenylmethanimine 

Downstream Products

• 81701-38-4 1-(3-chloro-2,3-diphenyl-1-cyclopropen-1-yl)naphthalene 
• 131269-28-8 5-Naphthalen-1-yl-6-phenyl-cyclopenta[b]thiophen-4-one 
• 131269-27-7 2-Phenyl-1-thiophen-2-yl-cyclopenta[a]naphthalen-3-one 
• 131269-29-9 2-Naphthalen-1-yl-3-thiophen-2-yl-inden-1-one 
• 452094-59-6 C₅H₄NCHCSn(C₄H₉)3C₁₀H₇ 
• 870009-47-5 1-(2-phenyl-1,2-dicarba-closo-dodecaboran-1-yl)naphthalene 
• 1240047-78-2 PhC(SnMe₃)C(C₆H₄-p-OMe)(1-naphthyl) 
• 1264837-09-3 1-(1-methylene-3-phenyl-1H-inden-2-yl)naphthalene 
• 1264837-08-2 1-(1-methylene-2-phenyl-1H-inden-3-yl)naphthalene 
• 2840-88-2 (Z)-1-styrylnaphthalene 
• 1403477-15-5 C₁₈H₁₃⁽²⁾H 
• 1403477-16-6 C₁₈H₁₃⁽²⁾H 
• 645-49-8 cis-stilben 
• 644-13-3 C₆H₅COC₁₀H₇ 

Relevant academic research and scientific papers

Sonogashira coupling in 3D-printed NMR cuvettes: synthesis and properties of arylnaphthylalkynes

3D-Printing has been used to build hollow NMR tube/spinner combinations out of NMR-transparent polyamide. The whole 3D-print has been processed inside a glove box and during pauses of the 3D-printing process, all reactants for the palladium-catalyzed deca

ONO pincer type binuclear Pd(II) complex: Synthesis, crystal structure and catalytic utilization of the resulting organopalladium complex in catalytic copper-free Sonogashira coupling reaction

New binuclear palladium (II) complex featuring ONO pincer type hydrazone ligand was synthesized and characterized by spectroscopic and single-crystal XRD analysis. This complex showed excellent catalytic activity towards the copper-free Sonogashira cross coupling reaction. The main advantages over previous methodologies include low catalyst loading, less problematic reaction media (H2O–DMSO) and reusability in homogenous systems for optimal performance.

Synthesis of Pd(II) large dinuclear macrocyclic complex tethered through two dipyridine-bridged aza-crowns as an efficient copper- and phosphine-free Sonogashira catalytic reaction

For the first time the new 32-membered macrocyclic dinuclear palladium complex of two aza-crown macrocycles, bearing two pyridine arms, Pd2L2Cl4 was synthesized and characterized by elemental analysis, IR, NMR spectroscopy and single crystal X-ray diffraction methods. Pd2L2Cl4 was investigated as a moisture/air-stable catalyst for Sonogashira cross-coupling reaction in the absence of copper and phosphine ligand in DMSO. Thermal stability, possible occurrence of tandem reactions, promoted catalytic performance as well as synergistic effects are of advantageous features of Pd2L2Cl4. By employing Taguchi method, optimum conditions (110 °C, 6 h, KOAc, 2 mol% cat.) were determined. Moreover, the homogenous catalyst represented good reusability up to four cycles. Comparing the catalytic activity of several other previously reported Pd(II) dinuclear complexes, Pd2L2Cl4 enjoys the advantages of short time of reaction and thermal stability.

High refractive index hyperbranched polymers with different naphthalene contents prepared through thiol-yne click reaction using di-substituted asymmetric bulky alkynes

In the present study, different aromatic moieties, naphthalene and benzene, were introduced into alkynes to constitute 1,3,5-tris(naphthylethynyl)benzene as B3 monomer. This monomer could be reacted with different ratios of hexane-1,6-dithiol (

One-pot Sonogashira–Hydroarylation reaction catalyzed by anionic palladium complexes in an aqueous medium

It was found that anionic Pd(II) complexes of type [CA]2[PdCl4] and [CA]2[Pd2Cl6] (CA = imidazolium or pyridinium cation) are effective catalysts for copper-free Sonogashira coupling in an aqueous med

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.]

Immobilized Pd on a NHC-functionalized metal-organic FrameworkMIL-101(Cr): An efficient heterogeneous catalyst in the heck and copper-free Sonogashira coupling reactions

A heterogeneous palladium catalyst system based on immobilization of palladium moieties on a N-heterocyclic carbene (NHC) modified metal organic framework (MOF) was developed for the Heck and copper-free Sonogashira coupling reactions. In order to prepare this catalyst system, first, MIL-101(Cr) was functionalized with NHC moieties through a post synthetic modification (PSM) approach, and then Pd metal was stabilized on the prepered MIL-101(Cr)-NHC substrate. This material was characterized using various microscopic and spectroscopic techniques and then was used as an efficient heterogeneous Pd catalyst system in the Heck and copper-free Sonogashira reactions. Results of the heterogeneity tests showed that the Pd-NHC-MIL-101(Cr) catalyst can efficiently catalyzed these coupling reactions heterogeneously and no remarkable changes observed in the morphology and structure of MIL-101(Cr) template during the reaction progress. Also, existence of palladium nanoparticles immobilized on the MOF structure affirmed by the TEM and XPS analysis confirmed the oxidation state of Pd. A variety of alkene and alkyne derivatives were synthesized in good to excellent yields using this heterogeneous Pd catalyst system under normal conditions. More importantly Pd-NHC-MIL-101(Cr) catalyst was simply recovered from the reaction medium without remarkable decreasing in its catalytic activities after five times of reusability. The ICP analysis showed the very low Pd and Cr metals leaching, representing high stability and applicability of this catalyst in Pd coupling reactions.

Ligand-free (: Z)-selective transfer semihydrogenation of alkynes catalyzed by in situ generated oxidizable copper nanoparticles

Herein, we present (Z)-selective transfer semihydrogenation of alkynes based on in situ generated CuNPs in the presence of hydrogen donors, such as ammonia-borane and a green protic solvent. This environmentally friendly method is characterized by operational simplicity combined with high stereo- and chemoselectivity and functional group compatibility. Auto-oxidation of CuNPs after the completion of a semihydrogenation reaction results in the formation of a water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need for any special regeneration processes. Formed NH4B(OR)4 can be easily transformed back into ammonia-borane or into boric acid. In addition, a one-pot tandem sequence involving a Suzuki reaction followed by semihydrogenation was presented, which allows minimization of chemical waste production.

Synthesis of N-Heterocyclic Carbine Silver(I) and Palladium(II) Complexes with Acylated Piperazine Linker and Catalytic Activity in Three Types of C—C Coupling Reactions

Two bis-imidazolium salts LH2·Cl2 and LH2·(PF6)2 with acylated piperazine linker and two N-heterocyclic carbene (NHC) silver(I) and palladium(II) complexes [L2Ag2](PF6)2 (1) and [L2Pd2Cl4] (2) were prepared. The crystal structures of LH2·Cl2 and 1 were confirmed by X-ray analysis. In 1, one 26-membered macrometallocycle was generated through two silver(I) ions and two bidentate ligands L. The catalytic activity of 2 was investigated in Sonogashira, Heck-Mizoroki and Suzuki-Miyaura reactions. The results displayed that these C—C coupling reactions can be smoothly carried out under the catalysis of 2.

Simple and efficient diaryl alkyne synthesis method

The embodiment of the invention discloses a simple and efficient diaryl alkyne synthesis method. The method comprises the steps of by taking arylmethylbenzotriazole and aromatic aldehyde as raw materials, carrying out addition and double-beta-elimination reaction under the action of bis (trimethylsilyl) amino salt MN (SiMe3) 2 to synthesize diaryl alkyne by a one-pot method. The raw materials and chemical reagents used in the method are easy to obtain, the reaction conditions are mild, the operation is simple, the substrate universality is good, the product yield is high, and the method is a simple and efficient diaryl alkyne synthesis method.