54737-49-4

Upstream product

• 5324-79-8 1-bromo-2-(phenylsulfonyl)benzene 
• 544-92-3 copper(I) cyanide 
• 15861-48-0 2-bromophenyl phenyl sulfide 
• 2905-25-1 o-bromobenzenesulfonyl chloride 
• 71-43-2 benzene 
• 4387-36-4 2-iodobenzonitrile 
• 873-55-2 sodium benzenesulfonate 
• 98-09-9 benzenesulfonyl chloride 
• 100-47-0 benzonitrile 
• 825-60-5 benzimidic acid ethyl ester 
• 114650-54-3 C₁₃H₉N₃S 
• 107046-32-2 C₁₂H₉ClN₂S 

Relevant academic research and scientific papers

Sequential C-H activation enabled expedient delivery of polyfunctional arenes

Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C-H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction of biologically active molecules, such as Bipenamol.

Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis

An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.

Visible-Light Photoredox/Nickel Dual Catalysis for the Cross-Coupling of Sulfinic Acid Salts with Aryl Iodides

An efficient cross-coupling of sodium or lithium sulfinates with aryl iodides, using a combination of nickel and photoredox catalysis, is described. The dual catalyst system enables a versatile synthesis of aryl sulfones at room temperature in good yields and displays a broad functional group compatibility. The potential utility of this method in the late-stage diversification of complex molecules and in the conversion of organolithium reagents and sulfur dioxide into sulfones is demonstrated.

Utilisation du cyanure de tetraethylammonium pour la preparation de complexes cyclopentadienyl fer cyclohexadienyl cyanes. Etude de leur oxydation electrochimique et chimique

Addition of tetraethylammonium cyanide to a solution of η5-cyclopentadienyl)(η6-arene)iron (1 +), in acetonitrile can be studied by voltammetry.With electron-withdrawing groups such as nitro, keto, sulfone, azo and azoxy bonded to the arene, the reaction occurs immediately and a wave resulting form oxidation of hexadienyl species is observed in the range 0-IV vs.SCE.Preparation of various hexadienyl compounds was achieved with good yields.In order to obtain ortho-substituted benzonitriles, electrochemical and chemical oxidations of hexadienyl complexes were compared.The best results were obtained with N-bromosuccinimide (NBS) and a demetallation generally occurs.A one-pot synthesis of benzonitrile compounds can be achieved after addition of cyanide ion and then NBS to a solution of (η5-cyclopentadienyl)(η6-arene) iron (1 +) in acetonitrile. 6-C6H5N(O)=NC6H4Cn-2>>+ is directly obtained from the azoxy dicationic compound 2+.Keywords: Iron; Ferrocenes; Electrochemistry; Arene complexes; Oxidation

1H and 13C NMR Study of Substituted Effects in 2- and 3-Substituted Diphenyl Sulphides and Sulphones and 4-Substituted 2',6'-Dimethyldiphenyl Sulphides

The proton and carbon NMR spectra of nine 2-substituted diphenyl sulphides (S-2-X), seven 3-substituted diphenyl sulphides (S-3-X), nine 2-substituted diphenyl sulphones (SO2-2-X), nine 3-substituted diphenyl sulphones (SO2-3-X) and nine 4-substituted-2',6'-dimethyldiphenyl sulphides (Me2-S-4-X) were obtained.Correlations of the 1H and 13C chemical shifts were made with benzene substituent-induced chemical shifts (Lynch plots) and Hammett and dual-substituent parameters and the results were compared with those of 4-substituted diphenyl sulphides (S-4-X) and sulphones (SO2-4-X).The main conclusions are as follows: (i) the transmission of the substituent effects in substituted diphenyl sulphides decreases in the order S-4-X ca.S-2-X > Me2-S-4-X > S-3-X; (ii) the inductive effects are transmitted to a larger extent than the resonance effects to the unsubstituted ring in 3-substituted diphenyl sulphides, while the reverse trend is observed in other substituted diphenyl sulphides; (iii) in 2-methoxy-, 2-chloro-, 2-bromo- and 2-nitrodiphenyl sulphides, an increase in the size of the substituent causes an upfield shift for H-6 ascribable to the repulsion between the lone pairs of electrons on the sulphur and the substituent and its influence on the conformation; (iv) the diminished transmission of substituent effects to the remote rings in 4-substituted 2',6'-dimethyldiphenyl sulphides is probably due to the orthogonal orientation of the rings; and (v) the signal due to the H-6 of 2-substituted diphenyl sulphones suffers a downfield shift with an increase in the size of the substituent, this being ascribable to the increasing steric interaction between the 2-substituent and the sulphonyl oxygen and consequent changes in the conformation. - Keywords: NMR; 1H NMR; 13C NMR; diphenyl sulphides; diphenyl sulphones; ?-polarization

A CONVENIENT SRN1 SYNTHESIS OF AROMATIC NITRILES FROM DIAZONIUM SALTS VIA DIAZOSULFIDES

Properly substituted diazosulfides XC6H4-N=N-SPh (1) (either isolated or generated in situ from arenediazonium tetrafluoroborates and sodium benzenethiolate) react with tetrabutylammonium cyanide, in Me2SO under photon or electron stimulation, leading to nitriles XC6H4CN (2).Satisfactory yields of 2, comparable with those of the Sandmeyer reaction, are obtained when X= 3- or 4-CF3, 2-, 3-, or 4-CN, 4-F, 4-MeCO, 3-MeO, 4-NO2, 4-PhCO, and 4-PhSO2.For different reasons, the reaction practically fails as a useful nitrile synthesis when X= H, 4-MeO, 2-, or 3-NO2.The collected evidences agree well with the intervention of an SRN1 mechanism to which diazosulfides 1, given their easy reducibility followed by a prompt fragmentation of the C-N and N-S bonds, are convenient participating substrates.An important consequence of the mechanism involved is the behaviour of bromo and chloro derivatives (1: X= Br, Cl) which lead, through the contemporaneous introduction of two cyano functionalities, to more than satisfactory yields of the corresponding dicyanobenzenes.

Antiarrhythmic agents. 2, 3, and 4 substituted benzylamines

The synthesis of a series of 2, 3, and 4 substituted benzylamine derivatives is described. These compounds were studied for their effect on experimental cardiac arrhythmias. Many of the derivatives, but in particular 2 (p methoxyphenylethynyl) benzylamine