55165-45-2

Upstream product

• 1885-29-6 anthranilic acid nitrile 
• 462-34-0 boron trifluoride-tetrahydrofuran complex 
• 7632-00-0 sodium nitrite 

Downstream Products

• 84451-30-9 2-cyano-tellurophenetole 
• 86436-75-1 C₁₄H₈N₂Te 
• 100-47-0 benzonitrile 
• 19096-31-2 2-phenyl-1H-inden-1-one 
• 37526-65-1 o-(Trifluormethylthio)-benzonitril 
• 73013-48-6 acetone 
• 107037-20-7 2-(phenylselanyl)benzonitrile 
• 135689-93-9 4-(2-Cyanophenyl)benzaldehyde 
• 100-52-7 benzaldehyde 
• 155395-45-2 2-(furan-2-yl)benzonitrile 
• 31656-77-6 2-azidobenzonitrile 
• 6609-54-7 2-cyanothioanisole 
• 121034-79-5 o-p-tolylsulfonylbenzonitrile 

Relevant academic research and scientific papers

Erythrosine B Catalyzed Visible-Light Photoredox Arylation–Cyclization of N-Alkyl-N-aryl-2-(trifluoromethyl)acrylamides to 3-(Trifluoromethyl)indolin-2-one Derivatives

3-Trifluoromethylindoline-2-one derivatives were prepared in a visible-light photocatalytic transformation of acrylamides. The arylation–cyclization sequence was initiated by light-induced aryl radical generation from aryldiazonium salts with the utilization of erythrosine B as an organic photocatalyst.

Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism

The first metal-free procedure for the synthesis of arylsulfonyl fluorides is reported. Under organo-photoredox conditions, aryl diazonium salts react with a readily available SO2 source (DABSO) to afford the desired product through simple nucleophilic fluorination. The reaction tolerates the presence of both electron-rich and -poor aryls and demonstrated a broad functional group tolerance. To shed the light on the reaction mechanism, several experimental techniques were combined, including fluorescence, NMR, and EPR spectroscopy as well as DFT calculations.

Modular and Selective Arylation of Aryl Germanes (C?GeEt3) over C?Bpin, C?SiR3 and Halogens Enabled by Light-Activated Gold Catalysis

Selective C (Formula presented.) –C (Formula presented.) couplings are powerful strategies for the rapid and programmable construction of bi- or multiaryls. To this end, the next frontier of synthetic modularity will likely arise from harnessing the coupling space that is orthogonal to the powerful Pd-catalyzed coupling regime. This report details the realization of this concept and presents the fully selective arylation of aryl germanes (which are inert under Pd0/PdII catalysis) in the presence of the valuable functionalities C?BPin, C?SiMe3, C?I, C?Br, C?Cl, which in turn offer versatile opportunities for diversification. The protocol makes use of visible light activation combined with gold catalysis, which facilitates the selective coupling of C?Ge with aryl diazonium salts. Contrary to previous light-/gold-catalyzed couplings of Ar–N2+, which were specialized in Ar–N2+ scope, we present conditions to efficiently couple electron-rich, electron-poor, heterocyclic and sterically hindered aryl diazonium salts. Our computational data suggest that while electron-poor Ar–N2+ salts are readily activated by gold under blue-light irradiation, there is a competing dissociative deactivation pathway for excited electron-rich Ar–N2+, which requires an alternative photo-redox approach to enable productive couplings.

Cascade annulations of aryldiazonium salts, nitriles and halo-alkynes leading to 3-haloquinolines

A regiospecific access to 3-haloquinolines has been developed via a three-component annulation of aryldiazonium salts, nitriles and haloalkynes. This reaction proceeds through an initial formation of reactive nitrilium ion and further cascade annulation with haloalkynes. This method provides a straightforward access to a diverse array of functionalized quinolones (28 examples) under mild conditions and exhibits broad functional group tolerance. Applications of this method in a gram scale reaction and a formal synthesis of Pitavastatin are illustrated.

An unprecedentedly simple method of synthesis of aryl azides and 3-hydroxytriazenes

Fischer's approach towards the synthesis of aryl azides and triazinoles from diazonium salts and hydroxylammonium chloride (phenylhydraxylamine) was reinvestigated and optimized. The new methodology enables the preparation of aryl azides and triazinoles in high yields in water at room temperature. The procedure is very simple, robust, easily scalable, reproducible, and "green".

One-Pot Reactions for Synthesis of 2,5-Substituted Tetrazoles from Aryldiazonium Salts and Amidines

One-pot sequential reactions of aryldiazonium salts with amidines followed by the treatment of I2/KI under basic conditions provide 2,5-disubstituted tetrazoles in moderate to excellent yields. This one-pot synthesis has several advantages such as mild reaction conditions, short reaction time, convenient workup, and high yields, making this methodology practical.

Aryldiazonium Tetrafluoroborate Salts as Green and Efficient Coupling Partners for the Suzuki-Miyaura Reaction: From Optimisation to Mole Scale

The use of aryldiazonium tetrafluoroborate salts as coupling partners in the Suzuki-Miyaura reaction was investigated from a process chemistry perspective including safety evaluation, solvent and catalyst screening and multivariate factor optimisation. Optimised conditions were applied to a range of substrates to evaluate the scope and limitations of the reaction, and one example was carried out on mole scale to demonstrate the practicality and scalability of the process.

Selective Reactions in the Triazene Series. Part 2. Protodediazoniation of Arenediazonium Salts with Formamide

Treatment of performed arenediazonium tetrafluoroborates or arenediazonium trifluoroacetates (formed in situ) with formamide an base effects reduction to the corresponding arene in moderate to good yield in cases where an electron-withdrawing substituent is present on the aromatic ring.Other functionalities remain unaffected.The mechanism of the protodediazoniation is shown to involve transfer of the formyl hydrogen atom to the substrate and may proceed via a 1-aryl-3-formyltriazine.