6775-17-3

Upstream product

• 859960-63-7 α-chloro-2,4-dinitro-stilbene 
• 13146-23-1 copper(I) phenylacetylenide 
• 584-48-5 2,4-dinitrobromobenzene 
• 331984-42-0 2-(benzo[d]thiazol-2-ylsulfonyl)-1-phenylethan-1-one 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 1226526-69-7 2-(5-chlorobenzothiazole-2-sulfonyl)-1-phenylethan-1-one 
• 1226526-89-1 2-(benzothiazole-2-sulfonyl)-2-(2,4-dinitro-phenyl)-1-phenyl-ethanone 
• 1226527-09-8 2-(5-chloro-benzothiazole-2-sulfonyl)-2-(2,4-dinitro-phenyl)-1-phenyl-ethanone 
• 536-74-3 phenylacetylene 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 99-65-0 meta-dinitrobenzene 

Downstream Products

• 6597-23-5 6-nitro-1-oxy-2-phenyl-indol-3-one 
• 58665-14-8 p-[1-benzoyl-1'-(2,4-dinitrophenyl)methane] 

Relevant academic research and scientific papers

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.

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.

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.

Direct synthesis of nitroaryl acetylenes from acetylenes and nitroarenes: Via oxidative nucleophilic substitution of hydrogen

Acetylenic carbanions add to nitroarenes (dinitrobenzenes, nitropyridines, etc.) to form σH-adducts that are subsequently oxidized by DDQ according to the oxidative nucleophilic substitution of hydrogen (ONSH) pathway to give nitroaryl acetylen

Synthesis, structure and catalysis of a NHC-Pd(II) complex based on a tetradentate mixed ligand

Bis-benzimidazolium salt (S)-2,2′-bis[2′′-(N-picolyl-benzimidazoliumyl)ethoxy]-1,1′-binaphthyl hexafluorophosphate [(S)-LH2]·(PF6)2 and its NHC palladium(ii) complex [(S)-LPd](PF6)2 (1) have been prepared and characterized. Complex 1 is formed by one tetradentate mixed ligand (S)-L and one Pd(ii) ion, in which one 15-membered ring and two 6-membered rings are present. In this complex, intramolecular π-π interactions between naphthalene rings and benzimidazole rings are observed. Additionally, the catalytic activity of complex 1 in three types of C-C coupling reactions (Suzuki-Miyaura, Heck-Mizoroki and Sonogashira reactions) was investigated. The results show that complex 1 is an effective catalyst in these coupling reactions.

Transition-metal-free formal sonogashira coupling and α-carbonyl arylation reactions

Transition-metal-free formal Sonogashira coupling and α-carbonyl arylation reactions have been developed. These transformations are based on the nucleophilic aromatic substitution (SNAr) of β-carbonyl sulfones to electron-deficient aryl fluorides, producing a key intermediate that, depending on the reaction conditions, gives the aromatic alkynes or α-aryl carbonyl compounds. The development of these reactions is presented and, based on investigations under basic and acidic conditions, mechanisms have been proposed. To develop the formal disclosed that expands the reaction concept. The scope of these reactions is demonstrated for the synthesis of Sonogashira and α-carbonyl arylated products from a range of electron-deficient aryl fluorides with a variety of functional groups and aryl-, heteroaryl-, alkyl-, and alkoxy-substituted sulfone nucleophiles. These transition-metal-free reactions complement the metal-catalyzed versions in terms of substitution patterns, simplicity, and reaction conditions.