15784-39-1

Upstream product

• 591-51-5 phenyllithium 
• 591-50-4 iodobenzene 
• 29079-00-3 4-ethynyl-1,1'-biphenyl 
• 589-87-7 1,4-bromoiodobenzene 
• 536-74-3 phenylacetylene 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 32340-38-8 biphenyl-4-yl-propynoic acid 
• 780-69-8 triethoxyphenylsilane 
• 3218-36-8 4-Phenylbenzaldehyde 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 150844-00-1 1-(biphenyl-4-yl)-2,2-dibromoethylene 
• 108-86-1 bromobenzene 
• 108-90-7 chlorobenzene 
• 92-92-2 biphenyl-4-carboxylic acid 

Downstream Products

• 111288-95-0 2',5'-diethyl-3',6'-diphenyl-p-quaterphenyl 
• 36803-53-9 1-([1,1′-biphenyl]-4-yl)-2-phenylethane-1,2-dione 
• 1522379-03-8 2-([1,1'-biphenyl]-4-yl)-4-phenylquinazoline 
• 95950-88-2 2-([1,1′-biphenyl]-4-yl)-3-phenylquinoxaline 
• 21175-18-8 (E)-4-phenylstilbene 
• 2039-69-2 (Z)-4-styryl-1,1'-biphenyl 
• 23934-48-7 2',5',3',6'-tetraphenyl-p-quaterphenyl 
• 111288-92-7 8-biphenylyl-7,10-di-n-hexyl-9-phenylfluoranthene 
• 111288-96-1 3',6'-diphenyl-2',5'-di-n-propyl-p-quaterphenyl 
• 111288-91-6 8-biphenyly-7,10-di-n-pentyl-9-phenylfluoranthene 

Relevant academic research and scientific papers

Immobilization of Pd catalysts on mesoporous silica for amine- and copper-free Sonogashira coupling reactions

Immobilization of catalysts on solid supports is a promising approach to combine the advantages of heterogeneous and homogeneous catalysts. Pd(PPh3)2Cl2, known as an extremely active homogeneous catalyst for the Sonogashira coupling reaction, has been immobilized on high-surface-area MCF (mesocellular foams)-type mesoporous silica powder modified with 3-aminopropyltriethoxysilane and subsequently with diphenylphosphine. The functionalized MCF-type silica and supported catalysts have been characterized by x-ray photoelectron spectroscopy (XPS), fourier transform infrared spectroscopy (FTIR), elemental analysis, nitrogen sorption porosimetry, and scanning electron microscopy (SEM). Such supported Pd catalysts have proven to be useful recyclable reagents for copper- and amine-free Sonogashira coupling reactions of haloaromatic compounds with terminal alkynes. Copyright Taylor & Francis Group, LLC.

Bis(NHC)-Pd-catalyzed one-pot competitive C-C*C-C, C-C*C-O, C-C*C-N, and C-O*C-N cross-coupling reactions on an aryl di-halide catalyzed by a homogenous basic ionic liquid (TAIm[OH]) under base-free, ligand-free, and solvent-free conditions

Bis(NHC)-Pd-catalyzed competitive asymmetrical C-C*C-C, C-C*C-O, C-C*C-N, and O-C*C-N cross-coupling reactions were performedviathe one-pot strategy in the presence of a new ionic liquid, which played the roles of solvent, base, and ligand simultaneously. The ionic liquid was prepared based on a methyl imidazolium moiety with hydroxyl counter anionsviaa Hofmann elimination on a 1,3,5-triazine framework (TAIm[OH]). Pd ions could be efficiently coordinated through the bis(NHC)-ligand moiety in the ionic liquid. Based on differences in the competitive kinetics of C-C cross-coupling reactions (Heck, Suzuki, and Sonogashira) with C-N and C-O cross-coupling reactions, and also differences in the kinetics of aryl halides, the coupling reactions could be selectively performed with a low amount of by-products. The competitive cross-coupling reactions were thus performed with high selectivity under mild reaction conditions.

One-Pot Dual C?C Coupling Reaction via Site Selective Cascade Formation by PdII-Cryptate of an Amino-Ether Heteroditopic Macrobicycle

Selectivity of aryl iodo over ethynyl iodo toward the Suzuki cross coupling reaction is explored by utilizing a palladium complex of amino-ether heteroditopic macrobicycle. Subsequently, unreacted ethynyl iodide undergoes homocoupling reaction in the same catalytic atmosphere, thereby representing a cascade dual C?C coupling reaction. Furthermore, this approach is extended for novel one-pot synthesis of unsymmetrical 1,3-diynes.

Selective Phosphoranation of Unactivated Alkynes with Phosphonium Cation to Achieve Isoquinoline Synthesis

We herein develop a selective phosphoranation of alkynes with phosphonium cation, which directs a concise approach to isoquinolines from unactivated alkyne and nitrile feedstocks in a single step. Mechanistic studies suggest that the annulation reaction is initiated by the unprecedented phosphoranation of alkynes, thus representing a unique reaction pattern of phosphonium salts and distinguishing it from existing protocols that largely rely on the utilization of highly functionalized imines/oximes and/or highly polarized alkynes.

Metal scavenging and catalysis by periodic mesoporous organosilicas with 2,2′-bipyridine metal chelating ligands

A periodic mesoporous organosilica containing 2,2′-bipyridine (BPy-PMO) was assessed as a metal scavenger and heterogeneous catalyst. The functionalized PMO was synthesized based on a modified version of a previously reported procedure and showed a large

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.

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.

Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes: Synthesis of unsymmetrical diarylethynes

Palladium/copper-cocatalyzed decarbonylative alkynylation of acyl fluorides with alkynylsilanes is described. This reaction not only effectively inhibits the formation of undesired homocoupled products by avoiding the addition of a base, but also exhibits a wide substrate scope to provide a general access to diverse unsymmetrical diarylethynes.

Palladium-catalyzed alkynylation of aromatic amines via in situ formed trimethylammonium salts

A palladium-catalyzed alkynylation of aromatic amines with terminal alkynes via in situ formed trimethylammonium salts is developed. Compared with previous system using ammonium salts as starting materials and high loading of pre-prepared NHC-Pd catalyst (10 mol% Pd), this reaction directly employed amines as the coupling partners and the commercially available Pd2(dba)3/PPh2Cy (1 mol% Pd) as the catalyst, greatly simplifying the manipulation and decreasing the cost.

Internal alkyne derivative and preparation method thereof

The invention belongs to the technical field of organic synthesis, and in particular relates to an internal alkyne derivative and a preparation method thereof. The first aspect of the application provides the internal alkyne derivative, wherein the struct