25699-92-7

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 120-72-9 indole 
• 623-26-7 terephthalonitrile 
• 1194-02-1 4-fluorobenzonitrile 
• 623-00-7 4-bromobenzenecarbonitrile 
• 3058-39-7 4-iodobenzonitrile 
• 874-90-8 4-methoxybenzonitrile 
• 619-72-7 4-nitrobenzonitrile 
• 31271-90-6 1-(p-toluenesulfonyl)-1H-indole 
• 77287-34-4 formamide 
• 174621-52-4 N-(4-bromophenyl)-1H-indole 
• 126747-14-6 4-cyanophenylboronic acid 
• 1477-50-5 Indole-2-carboxylic acid 

Downstream Products

• 71935-16-5 4-(1H-Indol-1-yl)Benzoic Acid 
• 16096-33-6 1-phenyl-1H-indole 
• 1443126-49-5 5-[4-(indol-1-yl)phenyl]-N,N-dimethyl-2H-tetrazole-2-carboxamide 
• 1443126-34-8 5-[4-(indol-1-yl)phenyl]tetrazole 
• 71935-17-6 1-(p-hydroxymethyl)phenylindole 

Relevant academic research and scientific papers

A Pd/Cu-Free magnetic cobalt catalyst for C-N cross coupling reactions: synthesis of abemaciclib and fedratinib

Herein, the synthesis of a nano-catalytic system comprising magnetic nanoparticles as the core and edible natural ligands bearing functional groups as supports for cobalt species is described. Subsequent to its characterization, the efficiency of the catalyst was investigated for C-N cross-coupling reactions using assorted derivatives of amines and aryl halides. This novel and easily accessible Pd- and Cu-free catalyst exhibited good catalytic activity in these reactions using γ-valerolactone (GVL) at room temperature; good recyclability bodes well for the future application of this strategy. The introduced catalytic system is attractive in view of the excellent efficiency in an array of coupling reactions and its versatility is illustrated in the synthesis of abemaciclib and fedratinib, which are FDA-approved new and significant anti-cancer medicinal compounds that are prepared under green reaction conditions.

Palladium-Catalyzed Cyanation of Aryl Halides Using Formamide and Cyanuric Chloride as a New “CN” Source

A new source of “CN” employing formamide and cyanuric chloride is introduced for the cyanation reactions. The treatment of formamide and 2,4,6-trichloro-1,3,5-triazine (TCT; cyanuric chloride) afforded an efficient cyanating agent which it can be used as a nontoxic, readily available, and non-expensive reagent in the cyanation transformations. In this study, palladium-catalyzed cyanation of aryl halides was successfully accomplished using this new “CN” source in high yields.

Exploration of Catalytic Activity of Quercetin Mediated Hydrothermally Synthesized NiO Nanoparticles Towards C–N Coupling of Nitrogen Heterocycles

Abstract: A new approach towards the preparation of phase pure NiO nanoparticles via quercetin mediated hydrothermal method is proposed in this work. The performance of quercetin as capping agent is found to be good. The XRD and SEM results confirm that the NiO nanoparticles prepared with quercetin are smaller in size and have refined morphology than that prepared without quercetin. Thermal stability, elemental composition and particle size of prepared nanoparticles have been revealed by TG-DSC, EDAX and HR-TEM analysis respectively. N2 adsorption–desorption isotherm (BET) analysis was done to reveal specific surface area. The prepared NiO nanoparticles act as cost effective, environmental friendly and efficient catalyst for the C–N cross coupling of indole and electron deficient pyrrole, under very mild reaction conditions. The catalytic system is able to tolerate many functional groups with different electronic and structural properties. Hence the present catalytic system may be possibly applied in large scale synthesis. Graphic Abstract: [Figure not available: see fulltext.].

Nickel-Catalyzed C-N Cross-Coupling of Ammonia, (Hetero)anilines, and Indoles with Activated (Hetero)aryl Chlorides Enabled by Ligand Design

The Ni(II) precatalyst (C1) featuring the phosphonite ancillary ligand Phen-DalPhos (L1) was employed in the cross-coupling of (hetero)anilines with (hetero)aryl chlorides and in the diarylation of ammonia with (hetero)aryl chlorides to afford heteroatom-dense di(hetero)arylamines. The PAd2-DalPhos precatalyst C4 provided complementary reactivity in cross-couplings of indoles with (hetero)aryl chlorides. Taken together, the demonstration of room-temperature reactivity within each of the reaction classes examined and the observation of useful chemoselectivity at low loading (≤0.5 mol % Ni) and on gram-scale distinguishes C1 and C4 from other metal catalysts (i.e., copper, palladium, nickel, or other) within the field of C-N cross-coupling chemistry.

Bulky 1,1′-Ferrocenyl Ligands Featuring Diazaphospholene or Dioxaphosphepine Donor Fragments: Catalytic Screening in Nickel-Catalyzed C-N Cross-Coupling

1,1′-Ferrocenyl ligands featuring either bulky dioxaphosphepine (L1) or diazaphospholene (L2) donor moieties have been prepared, crystallographically characterized, and tested in representative nickel-catalyzed C–N cross-coupling reactions. Ligand L1 prov

Nickel-catalyzed decarbonylation of: N -acylated N-heteroarenes

Nickel-catalyzed decarbonylation of N-acylated N-heteroarenes is developed. This method can be used to produce a variety of N-aryl heteroarenes, including pyrroles, indoles, carbazoles and phenoxazines, using benzoic acid derivatives as arylating reagents. Arylnickelamide intermediates that are relevant to the catalytic reaction were characterized by X-ray crystallography. When N-acylated benzimidazoles are used as substrates, decarbonylation accompanied 1,2-migration to form 2-arylated benzimidazoles.

Copper-Catalyzed Decarboxylative N -Arylation of Indole-2-carboxylic Acids

A novel decarboxylative N -arylation of indole-2-carboxylic acids with aryl halides is developed. The reaction proceeds efficiently in the presence of Cu 2 O as the catalyst to give the corresponding N -aryl indoles in high yields. This synthet

Evaluating 1,1′-Bis(phosphino)ferrocene Ancillary Ligand Variants in the Nickel-Catalyzed C-N Cross-Coupling of (Hetero)aryl Chlorides

Previous reports in the literature have established the utility of 1,1′-bis(diphenylphosphino)ferrocene (DPPF, LPh) in the nickel-catalyzed cross-coupling of (hetero)aryl electrophiles with primary or secondary amines. In an effort to evaluate

Thieme Chemistry Journals Awardees - Where Are They Now? Efficient Cross-Coupling of Secondary Amines/Azoles and Activated (Hetero)Aryl Chlorides Using an Air-Stable DPEPhos/Nickel Pre-Catalyst

Synthesis and characterization of the new air-stable pre-catalyst (DPEPhos)Ni(2-mesityl)Br (C1) is reported, along with the application of this pre-catalyst in the cross-coupling of secondary amines/azoles with activated (hetero)aryl chlorides to afford t

Formation of C-C, C-S and C-N bonds catalysed by supported copper nanoparticles

Transition-metal catalysed cross-coupling reactions are still dominated by palladium chemistry. Within the recent past, copper has gained ground against palladium by virtue of its cheaper price and equivalent function in certain reactions. Four catalysts consisting of copper nanoparticles on zeolite, titania, montmorillonite and activated carbon have been tested in three palladium- and ligand-free cross-coupling reactions to form carbon-carbon, carbon-sulfur and carbon-nitrogen bonds. CuNPs/zeolite has been found to be the best one in the Sonogashira reaction of aryl iodides and arylacetylenes, as well as in the coupling of aryl halides with aryl and alkyl thiols, being reusable in both cases. However, the arylation of nitrogen-containing heterocycles (imidazole, pyrazole, benzimidazole and indole) has been better accomplished with CuNPs/titania, albeit CuNPs/activated carbon showed better recycling properties. The catalytic activity of the nanostructured catalysts has been compared with that of twelve commercial copper catalysts, with the former outperforming the latter in the three types of reactions studied.