62856-42-2

Upstream product

• 766-96-1 4-bromo-1-ethynylbenzene 
• 539-44-6 N-4-methylphenylhydrazine 
• 589-87-7 1,4-bromoiodobenzene 
• 766-97-2 4-n-methylphenylacetylene 
• 112176-19-9 triisopropoxy(4-methylphenyl)titanium 
• 934-94-1 1-bromo-4-bromoethynyl-benzene 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 98-59-9 p-toluenesulfonyl chloride 
• 5467-74-3 4-Bromophenylboronic acid 
• 5720-05-8 4-methylphenylboronic acid 
• 136350-66-8 1-bromo-4-(2,2-dibromovinyl)benzene 
• 624-31-7 4-tolyl iodide 

Downstream Products

• 252960-45-5 4-[2-[4-[2-(4-methylphenyl)ethynyl]phenyl]ethynyl]benzonitrile 
• 114794-88-6 1-[2-(4-methylphenyl)ethynyl]-4-(2-phenylethynyl)benzene 
• 40396-75-6 1-(4-bromophenyl)-2-(4-methylphenyl)-1,2-ethanedione 
• 62856-31-9 (E)-1-(4-bromophenyl)-2-p-tolylethene 
• 1403495-59-9 3,4-bis(4-bromophenyl)-1-phenyl-2,5-di(p-tolyl)-1H-pyrrole 
• 1403495-57-7 2,5-bis(4-bromophenyl)-1-phenyl-3,4-di(p-tolyl)-1H-pyrrole 
• 1403495-58-8 2,4-bis(4-bromophenyl)-1-phenyl-3,5-di(p-tolyl)-1H-pyrrole 
• 1403495-33-9 C₂₁H₁₆BrN 
• 1403495-34-0 C₂₁H₁₆BrN 
• 1383663-75-9 (Z)-1-(2-(4-bromophenyl)-1-p-tolylvinyl)-1H-indole 
• 1383663-74-8 (E)-1-(2-(4-bromophenyl)-1-p-tolylvinyl)-1H-indole 
• 1357155-22-6 1-(2-(4-bromophenyl)-1-(p-tolyl)vinyl)-3-methyl-1H-indole 

Relevant academic research and scientific papers

Palladium-catalyzed Sonogashira and Hiyama reactions using phosphine-free hydrazone ligands

(Chemical Equation Presented) Palladium/copper-catalyzed Sonogashira cross-coupling reaction of aryl halides with a variety of terminal alkynes under amine-free conditions in dimethylformamide (DMF) at 80 °C gave internal arylated alkynes using PdCl2(MeCN)2 with phosphine-free hydrazone 2a as a ligand and CuI as the cocatalyst in good yields. We also found PdCl2/hydrazone ligand 1d in PhMe at 80°C was a phosphine-free efficient catalyst system for a Hiyama cross-coupling reaction of aryl bromides with aryl(trialkoxy)silanes in good yields.

Highly efficient synthesis of 1,2-disubstituted acetylenes derivatives from the cross-coupling reactions of 1-bromoalkynes with organotitanium reagents

A Highly efficient route for the synthesis of 1,2-disubstituted acetylene derivatives has been developed by nickel catalyzed cross-couplings of alkynyl halides with aryl titanium reagents under mild conditions. This has given corresponding cross-coupling products good to excellent isolated yields of up to 92 %. The aryls bearing electron-donating or electron-withdrawing groups in either alkynylhalides or aryltitanium substrates gave cross-coupling products good yields. This process was simple and easily performed, which provides an efficient method for the synthesis of 1,2-disubstituted acetylenes derivatives.

Alkynyl?B(dan)s in Various Palladium-Catalyzed Carbon?Carbon Bond-Forming Reactions Leading to Internal Alkynes, 1,4-Enynes, Ynones, and Multiply Substituted Alkenes

It was found that the C(sp)?B(dan) bond of alkynyl?B(dan)s can be directly used for palladium-catalyzed carbon?carbon bond-forming reactions with aryl(alkenyl) halides and allylic carbonates as electrophiles, thus delivering unsymmetrical internal alkynes and unconjugated 1,4-enynes, respectively. With acyl chlorides as electrophiles, ynone synthesis is also promoted by a palladium catalyst with the assistance of a copper co-catalyst. These reactions can be achieved as more convenient one-pot reactions, without isolating the alkynyl?B(dan) formed in situ by the zinc-catalyzed dehydrogenative borylation of alkynes with HB(dan). In addition to direct C(sp)?B(dan) bond transformations, the C≡C bond in an alkynyl?B(dan) proved to be a promising scaffold for the construction of a multisubstituted alkene, which is synthesized by diboration of the C≡C?B(dan) moiety, leading to a triborylalkene followed by iterative regio- and stereoselective Suzuki?Miyaura cross-coupling reactions. As one example, the synthesis of the ethene with four different aryl groups, p-MeC6H4, p-MeOC6H4, p-NCC6H4, and p-F3CC6H4, was attained in high overall yield of 64% in six steps starting from the terminal alkyne, p-MeC6H4C≡CH. Besides these synthetic applications of the alkynyl?B(dan), the scope of the alkynyl substrate in the zinc-catalyzed dehydrogenative borylation was expanded to enhance the reliability as a provider of the alkynyl?B(dan). Consequently, 42 alkynes were found to participate in the dehydrogenative borylation as substrates; these are alkyl-, alkenyl-, aryl-, heteroaryl-, ferrocenyl-, silyl-, and borylalkynes, with or without a variety of functional groups. Lastly, a new method for preparing HB(dan), as a sulfide-free, cost-saving, and reaction-time-saving route, is disclosed. (Figure presented.).

Achieving non-doped deep-blue OLEDs by applying bipolar imidazole derivatives

In this work, we designed and synthesized two novel bipolar deep-blue emitting materials, 2-(4'-(9H-carbazol-9-yl)-[1,1′-biphenyl]-4-yl)-1 (4(tri-fluoromethyl) phenyl)-1H-phenanthro[9,10-d] imidazole (CzB-FMPPI) and 9-(4'-(4,5-diphenyl-1 (4-(trifluoromethyl) phenyl)-1H-imidazole-2-yl)-[1,1′-biphenyl]-4-yl)-9H-carbazole (CzB-FMPIM). Among them, carbazole and phenanthroimidazole are bridged linkage by the biphenyl ring and act as electron-donating part. The CF3-substituted phenyl ring applies as strong electron-withdrawing moiety. The exhibit highly twisted molecular configuration of two compounds efficiently shorten π-conjugation and inhibit intermolecular interaction, resulting in superior thermal stability and deep blue emission. High decomposition temperature of 431 °C and 414 °C, glass transition temperature of 150 °C and 135 °C for CzB-FMPPI and CzB-FMPIM, respectively, had been achieved. As a consequence of breaking the conjugation of phenanthroimidazole chromophore, CzB-FMPIM achieves an 8 nm blue-shifted emission compared with CzB-FMPPI. CzB-FMPPI exhibits a higher relative fluorescence quantum yield of 92.5% than 83.3% of CzB-FMPIM. Moreover, bipolar property was observed in both compound and homogeneous amorphous films were deposited and applied in the non-doped deep-blue OLEDs. The devices based on two emitters showed maximum luminance of 6667 cd/m2 and 3084 cd/m2, maximum EQE of 4.10% and 3.17%, respectively. Commission International de l'éclairage (CIE) coordinates of CzB-FMPIM based device achieved (0.15, 0.07) which is extremely close to the NTSC standard blue CIE (0.14, 0.08).

Palladium-Catalyzed Desulfitative Cross-Coupling of Arylsulfonyl Hydrazides with Terminal Alkynes: A General Approach toward Functionalized Internal Alkynes

A palladium-catalyzed Sonogashira-type coupling between arylsulfonyl hydrazides and terminal alkynes via Ar(C)-S bond cleavage is disclosed, which enables the general synthesis of functionalized internal alkynes, especially the Br-substituted ones, in good to excellent yields under acid- and base-free conditions.

Polymer anchored 3-benzoyl-1-(1-benzylpiperidin-4-yl)-2-thiopseudourea-Pd(II) complex: An efficient catalyst for the copper and solvent free Sonogashira cross-coupling reaction

An efficient copper and solvent free Sonogashira cross-coupling reaction catalyzed by polymer supported 3-benzoyl-1-(1-benzylpiperidin-4-yl)-2-thiopseudourea-Pd(II) complex 4 (PS-bpt-Pd) was reported. This inexpensive and simply synthesized heterogeneous catalyst 4 afforded excellent yields of the cross-coupling products under mild reaction conditions. We have achieved high yields for aryl iodide coupling reactions with terminal alkynes at room temperature under copper and solvent-free conditions. In addition, we also observed moderate to good yields for aryl bromides as coupling partner. This insoluble PS-bpt-Pd(II) catalyst 4 can be easily recovered by simple filtration and reused up to five times with stable catalytic activity. In addition to this, heterogeneous Pd (II) complex is even applicable on a gram scale for cross-coupling with high catalytic efficiency.

Palladium-catalyzed aerobic oxidative cross-coupling of arylhydrazines with terminal alkynes

The palladium-catalyzed Sonogashira-type aerobic oxidative coupling of arylhydrazines with terminal alkynes via C-N bond cleavage has been developed; internal alkynes were afforded with a broad substrate scope. This reaction proceeds under copper- and base-free conditions with molecular oxygen as the sole oxidant and nitrogen and water as the only by-products.

Recyclable and reusable NiCl2(PPh3)2/CuI/PEG-400/H2O system for the sonogashira coupling reaction of aryl iodides with alkynes

A stable and highly efficient NiCl2(PPh3)2/CuI/PEG-400/H2O catalytic system for the Sonogashira reaction has been developed. In the presence of NiCl2(PPh3)2 and CuI, the coupling reaction of aryl iodides with terminal alkynes was carried out smoothly in a mixture of poly(ethylene glycol) (PEG-400) and water at 100C with K2CO3 as base to afford a variety of arylacetylenes in good to excellent yields. The isolation of the products was readily performed by extraction with petroleum ether, and the NiCl2(PPh3)2/CuI/PEG-400/H2O system could be easily recycled and reused six times without significant loss of catalytic activity. Our system not only avoids the use of easily volatile organic solvents but also solves the basic problem of catalyst reuse.

Melamine-based microporous network polymer supported palladium nanoparticles: A stable and efficient catalyst for the sonogashira coupling reaction in water

A template consisting of a melamine-based microporous polymer network was synthesized and utilized as a solid support to stabilize palladium nanoparticles; the resulting Pd/SNW1 material showed good catalytic activity in copper-free Sonogashira coupling in water. Various aryl iodides were efficiently coupled with arylacetylenes under very low catalyst loadings in an environmentally benign medium. Hot filtration tests confirmed the heterogeneity of the catalyst, which was reused under the optimized conditions without any significant change in its activity. This simple preparation of the catalyst, the stability of the catalyst, product selectivity, and easy recovery and regeneration indicate the possible utilization of this catalytic system in a multitude of catalyzed reactions and industrial processes. Networking possibilities: A template consisting of melamine-based microporous polymer network is synthesized and utilized as a solid support to stabilize palladium nanoparticles; the resulting Pd/SNW1 material shows good catalytic activity in copper-free Sonogashira coupling in water. Various aryl iodides are efficiently coupled with arylacetylenes under very low catalyst loadings in an environmentally benign medium.

Pd-tetrahydrosalan-type complexes as catalysts for sonogashira couplings in water: Efficient greening of the procedure

New sulfonated tetrahydrosalen-type ligands and their water-soluble palladium(II) complexes have been synthesized. The palladium(II) complexes catalyze the Sonogashira coupling (23 examples) of various aryl halides (including chloroarenes) with terminal alkynes, with good to excellent conversions under mild conditions (80 °C, air, no CuI cocatalyst) in aqueous-organic mixtures and turnover frequencies of up to 2790 h -1. Under optimized reaction conditions to minimize environmental contamination, diphenylacetylenes can be isolated in 76-98 % yield. The aqueous catalyst solution can be recycled four times with decreasing activity; however, yields between 93 and 98 % can still be achieved with extended reaction times. Several water-insoluble products can be isolated in excellent yield by simple filtration and purification by washing with water; this method is used, for the first time, for this type of C - C coupling procedure.