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Upstream product

• 13329-40-3 4-Iodoacetophenone 
• 766-97-2 4-n-methylphenylacetylene 
• 624-31-7 4-tolyl iodide 
• 75883-03-3 4'-(2-trimethylsilylethynyl)acetophenone 
• 99-90-1 para-bromoacetophenone 
• 536-74-3 phenylacetylene 
• 1086430-08-1 1-[4-(iodoethynyl)phenyl]ethanone 
• 5720-05-8 4-methylphenylboronic acid 
• 40667-81-0 (4-methylphenyl)gold(triphenylphosphine) 
• 149104-90-5 4-acetylphenylboronic acid 
• 863098-32-2 1-(4-(bromoethynyl)phenyl)-ethan-1-one 
• 106-38-7 para-bromotoluene 
• 471-25-0 Propiolic acid 
• 99-92-3 p-aminobenzophenone 

Relevant academic research and scientific papers

A novel zinc-catalyzed Suzuki-type cross-coupling reaction of aryl boronic acids with alkynyl bromides

A novel Suzuki-type cross-coupling reaction of organoboron reagents with alkynyl bromides has been developed in the presence of catalytic Et2Zn/DMEDA system. The reaction afforded a variety of internal alkynes in moderate to excellent yields under mild reaction conditions without the formation of any homo-coupling products. The resulting internal alkynes have valuable applications in pharmaceutical and industrial areas. The use of relatively non-toxic zinc, chelating amine ligand and low reaction temperature make this protocol an alternative for the synthesis of internal alkynes. The scope and limitations of this protocol are also investigated.

Synthesis, Crystal Structures, and Catalytic Application of Two Triphenylphosphine-Cyclopalladated Ferrocenylpyrazine Complexes Containing Chlorine/Iodine Anion

Two new triphenylphosphine-cyclopalladated ferrocenylpyrazine complexes containing chlorine/iodine anion 2-3 have been easily prepared from the bridge-splitting reaction of the palladacyclic dimer 1 and anion exchange reaction, respectively. They were characterized by elemental analysis, IR, and 1H NMR. Additionally, the structures of these two complexes were determined by single-crystal X-ray analysis and C-H···N hydrogen bonds and π-π interactions were found in the their crystal structures. These complexes displayed good activity in the coupling of terminal alkynes with arylboronic acids under atmospheric conditions. This method provided the corresponding arylalkynes with good to excellent yields.

Nickel-Catalyzed Hiyama-type Decarboxylative Coupling of Propiolic Acids and Organosilanes

A Ni catalytic system was developed for the decarboxylative coupling reaction of alkynyl carboxylic acids with organosilanes. Ni(acac)2 and 1,10-phenanthroline showed the best result in the presence of CsF and CuF2 at 120 °C. This system tolerated the presence of alkyl, alkoxy, halogen, nitro, cyano, ketone, and ester functional groups. Moreover, the reaction with but-2-ynedioic acid and organosilane afforded the corresponding symmetrical diarylalkynes.

Copper- and ligand-free Sonogashira reaction catalyzed by Pd(0) nanoparticles at ambient conditions under ultrasound irradiation

The Sonogashira reaction proceeds at ambient temperature (30°C) in acetone or room-temperature ionic liquid, 1,3-di-n-butylimidazolium tetrafluoroborate ([bbim]BF4), as solvent under ultrasound irradiation to give enhanced reaction rates, excellent chemoselectivity, and high yields in the absence of a copper cocatalyst and a phosphine ligand. TEM analysis showed the formation of stable, crystalline, and polydispersed Pd(0) nanoparticles as catalyst for the reaction.

Inside-out core-shell architecture: Controllable fabrication of Cu 2O@Cu with high activity for the Sonogashira coupling reaction

Inside-out core-shell architectures (Cu2O@Cu) with a Cu 2O core and a Cu shell, which are in contrast to the normally reported Cu2O-outside structure (Cu@Cu2O), were fabricated. This strategy can also be applied

Effective palladium(II)-bis(oxazoline) catalysts: Synthesis, crystal structure, and catalytic coupling reactions

New bis(oxazoline) ligands and their palladium complexes were synthesized and characterized. X-ray crystal structures of the two new complexes showed distorted square planar geometry with the palladium ion bonded to nitrogens of two bidentate heterocycles in addition to two bromides and two acetate ions for Pd-BOX-1 and Pd-BOX-2, respectively. The complexes adopt a chair structure with a rigid curvature inducing an inherent chirality. The complexes were effective catalysts for Suzuki-Miyaura, Mizoroki-Heck, and copper-free Sonogashira coupling reactions in aqueous dimethylformamide and under aerobic conditions. The reaction conditions were optimized for best solvent, base, and temperature. The substrate scope of the new catalytic system was evaluated for coupling reactions of a variety of aryl halides with aryl boronic acids, alkenes, and alkynes.

Copper-free Sonogashira cross-coupling reaction catalyzed by polymer-supported N-heterocyclic carbene palladium complex

A core-shell type of polymer-supported N-heterocyclic carbene (NHC) palladium catalyst was applied to Sonogashira cross-coupling reactions without copper cocatalyst under ambient atmosphere. This supported NHC-palladium complex efficiently catalyzed the c

Role of substituents present in bidentate ligand frame of Cu(I) catalysts on Sonogashira cross coupling reactions

Cu(I) catalysts {[Cu(L1?4)Cl(PPh3)] where L1?4 = condensed product of 2-(1-phenylhydrazinyl)-pyridine with different benzaldehydes} were synthesized and characterized by 1H NMR, 31P NMR, UV–Vis and IR techniques. Complex 2 structure was authenticated by single crystal X-ray method. Different electron donating and withdrawing substituents are present in the ligand frame of Cu(I) catalysts and their role on Sonogashira reaction was investigated. The efficiency order of catalysts for the coupling reaction was found to be 2 > 1>3 > 4, clearly indicated the role of substituents present in the ligand frame was useful to effectively catalyze the Sonogashira reaction. The products were characterized using 1H NMR and 13C NMR.

Efficient synthesis of unsymmetric diarylalkynes from decarboxylative coupling in a continuous flow reaction system

Unsymmetric diaryl alkynes were synthesized from the palladium-catalyzed decarboxylative coupling of aryl halides and propiolic acid using a continuous flow reaction system. This flow chemistry system continuously gave the desired products in moderate to good yields, and produced less byproduct than was formed in the batch reaction.

A Waste-Minimized Approach to Cassar-Heck Reaction Based on POLITAG-Pd0 Heterogeneous Catalyst and Recoverable Acetonitrile Azeotrope

Three different Pd0-based heterogeneous catalysts were developed and tested in the Cassar–Heck reaction (i. e., copper-free Sonogashira reaction) aiming at the definition of a waste minimized protocol. The cross-linked polymeric supports used in this investigation were designed to be adequate for different reaction media and were decorated with different pincer-type ionic ligands having the role of stabilizing the formation and dimension of palladium nanoparticles. Among the ionic tags tested, bis-imidazolium showed the best performances in terms of efficiency and durability of the metal catalytic system. Eventually, aqueous acetonitrile azeotrope was selected as the reaction medium as it allowed the best catalytic efficiency combined with easy recovery and reuse. Finally, the synergy between the selected catalyst and reaction medium allowed to obtain highly satisfactory isolated yields of a variety of substrates while using a low amount of metal catalyst. The high performance of the designed POLymeric Ionic TAG (POLITAG)-Pd0, along with its good selectivity achieved in a copper-free process, also led to a simplified purification procedure allowing the minimization of the waste generated as also proven by the very low E-factor values (1.4–5) associated.