201278-01-5

Upstream product

• 287935-95-9 (3,5-dimethylphenyl)trimethoxysilane 
• 536-74-3 phenylacetylene 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 637-44-5 phenylpropyolic acid 
• 556-96-7 5-bromo-1,3-xylene 
• 5075-59-2 diethyl(phenylethynyl)aluminum 
• 1342307-08-7 3,5-dimethylphenyl 1H-imidazole-1-sulfonate 
• 34696-73-6 3,5-dimethyphenylmagnesium bromide 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 591-50-4 iodobenzene 
• 22445-41-6 3,5-dimethylphenyl iodide 
• 1137088-28-8 (3,5-dimethylphenyl)(triphenyl-λ5-phosphanyl)gold 

Downstream Products

• 329937-72-6 C₁₆H₁₇NO 
• 1452220-11-9 1-(3,5-dimethylphenyl)-2-phenylethane-1,2-dione 
• 40477-38-1 (Z)-1-(3,5-dimethylphenyl)-2-phenylethene 
• 1142802-64-9 Cp₂Zr[2,4-Ph₂-3,5-(3,4-dimethylphenyl)C₄] 
• 1142802-67-2 Cp₂Zr[2,5-Ph₂-3,4-(3,4-dimethylphenyl)C₄] 
• 1142802-62-7 Cp₂Zr[3,4-Ph₂-2,5-(3,4-dimethylphenyl)C₄] 
• 86846-72-2 1,3-dimethyl-5-phenethylbenzene 

Relevant academic research and scientific papers

Sub-Mol % catalyst loading and ligand-acceleration in the coppercatalyzed coupling of aryl Iodides and terminal alkyenes

(Figure Presented) Just add ligand! The coupling of aryl iodides and terminal alkynes can be catalyzed with sub-mol % amounts of a copper complex. Addition of a large excess of diamine ligand converts the inactive polymeric resting state of the catalyst i

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.

Cu2O Nanocrystals-Catalyzed Photoredox Sonogashira Coupling of Terminal Alkynes and Arylhalides Enhanced by CO2

Herein the first visible-light-activated Sonogashira C?C coupling reaction at room temperature catalyzed by single-metal heterogeneous Cu2O truncated nanocubes (Cu2O TNCs) was developed. A wide variety of aryl halides and terminal alkynes worked well in this recyclable heterogeneous photochemical process to form the corresponding Sonogashira C?C coupling products in good yields. Mechanistic control studies indicated that CO2 enhances the formation of light-absorbing heterogeneous surface-bound CuI-phenylacetylide (λmax=472 nm), which further undergoes single-electron transfer with aryl iodides/bromides to enable Sonogashira Csp2 ?Csp bond formation. In contrast to literature-reported bimetallic TiO2-containing nanoparticles as photocatalyst, this work avoided the need of cocatalysis by TiO2. Single-metal CuI in Cu2O TNCs was solely responsible for the observed Csp2 ?Csp coupling reactions under CO2 atmosphere.

Enhanced catalytic activity of CuI/diethoxyphosphoryl-1,10-phenanthrolines in ‘on water’ Cu-catalyzed Sonogashira reaction

The use of CuI/diethoxyphosphoryl-1,10-phenanthrolines and ‘on water’ conditions in the Cu-catalyzed Sonogashira reaction of aryl iodides with terminal alkynes significantly increases the reaction rate as compared to that in organic solvents.

Supramolecular ensemble of a TICT-AIEE active pyrazine derivative and CuO NPs: A potential photocatalytic system for sonogashira couplings

The donor-acceptor system 4 having pyrazine scaffold as an acceptor moiety coupled to donor amino groups through rotatable phenyl rings has been synthesized, which formed aggregates in aqueous media, exhibited copper induced restriction to intramolecular rotation, and served as a "not quenched" probe for the detection of copper(II) ions. During this process, the aggregates of derivative 4 acted as reactors and stabilizers for the generation of CuO NPs and themselves became oxidized to form polyamine derivative 6. Interestingly, the oxidized species 6 in combination with copper oxide nanoparticles served as light-harvesting antennas and exhibited excellent photocatalytic efficiency in Sonogashira coupling under mild and eco-friendly conditions (room temperature, aqueous media, aerial conditions, and visible light irradiation).

Single electron transfer-induced coupling of alkynylzinc reagents with aryl and alkenyl iodides

Alkynylzinc reagents were found to undergo coupling with aryl and alkenyl iodides to give arylalkynes and alkenylalkynes without the aid of transition metals. The coupling reaction proceeds through a single electron transfer mechanism, where a substoichiometric amount of a phosphine works as an indispensable activator.

An efficient zinc-catalyzed cross-coupling reaction of aryl iodides with terminal aromatic alkynes

The first Zn-catalyzed protocol for C(sp2)-C(sp) cross-coupling reactions for the synthesis of disubstituted alkynes is described. A broad spectrum of functional groups is tolerated during the catalysis and successfully afforded a variety of di

The copper-free Sonogashira cross-coupling reaction promoted by palladium complexes of nitrogen-containing chelating ligands in neat water at room temperature

The commercially available 2,2′-dipyridylamine was used as a supporting ligand in the palladium-catalyzed Sonogashira cross-coupling reaction. The reactions between aryl iodides and terminal alkynes with different steric hindrance can be efficiently performed in the absence of copper in neat water at room temperature. The superior catalytic performance of the catalytic system was attributed to water solubility of the palladium 2,2′- dipyridylamine complex. Palladium nanoparticles with small size and narrow size distribution were formed after the cross-coupling reaction.

Nickel-catalyzed cross-coupling reaction of alkynyl bromides with Grignard reagents

We describe a convenient method for the synthesis of 1,2-disubstituted acetylenes via a cross-coupling reaction of (bromoethynyl)benzene with Grignard reagents. The reaction of (bromoethynyl)benzene (1 mmol) with Grignard reagent (1.3 mmol) mediated by NiCl2 (4 mol%) and (p-CH3Ph)3P (8 mol%) in THF could produce 1,2-disubstituted acetylenes in good yields at room temperature.

Pd/tetraphosphine catalytic system for Cu-free Sonogashira reaction "on water"

An efficient copper-free Sonogashira coupling reaction was performed on water at 100 °C with N,N,N′,N′-tetra(diphenylphosphinomethyl) pyridine-2,6-diamine (1) as a ligand, [Pd(η3-C3H 5)Cl]2 as a catalyst precursor and K3PO 4 as a base. Both aryl and heteroaryl halides were successfully alkynylated in this system, and a high turnover number (TON) up to 860000 was obtained with a catalyst loading as low as 1 ppm.