219915-65-8

Upstream product

• 58061-82-8 4-(butylthio)benzenamine 
• 151-50-8 potassium cyanide 
• 109-79-5 n-butanethiol 
• 66107-32-2 4-cyanophenyl trifluoromethanesulfonate 
• 2863-98-1 4-hydrazinobenzonitrile hydrochloride 
• 629-45-8 dibutyl disulfide 
• 623-00-7 4-bromobenzenecarbonitrile 
• 3058-39-7 4-iodobenzonitrile 
• 109-69-3 n-Butyl chloride 

Downstream Products

• 36602-01-4 4-(phenylamino)benzonitrile 
• 105041-54-1 4-butylsulfanyl-benzoyl chloride 
• 22683-49-4 4-butylthio benzoic acid 

Relevant academic research and scientific papers

Ullmann-type: N-arylation of anilines with alkyl(aryl)sulfonium salts

A palladium/copper-cocatalyzed Ullmann-type N-arylation of anilines using alkyl(aryl)sulfonium triflates as arylation reagents has been accomplished. The reaction enabled Caryl-S bond cleavage over Calkyl-S bond breakage of alkyl(aryl)sulfoniums by Pd(P(tBu)3)2/CuI and gave the corresponding N-arylated products in good to high yields. It was also significant that the reactions of aniline with asymmetric butyl(mesityl)(aryl)sulfonium triflates showed excellent selectivity, in which the aryl groups other than the bulky and electron-rich mesityl moieties were transformed.

Electrochemically Promoted Nickel-Catalyzed Carbon-Sulfur Bond Formation

This work describes a nickel-catalyzed Ullmann-type thiolation of aryl iodidesunder mild electrochemical conditions. The simple undivided cell with graphene/nickel foam electrode setups offers excellent substrate tolerance, affording aryl and alkyl sulfides in good chemical yields. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated by cyclic voltammetry.

Visible-Light-Mediated Synthesis of Unsymmetrical Diaryl Sulfides via Oxidative Coupling of Arylhydrazine with Thiol

A metal-free visible-light-promoted oxidative coupling between thiols and arylhydrazines has been developed to afford diaryl sulfides using a catalytic amount of rose bengal as photocatalyst under aerobic conditions. A library of unsymmetrical diaryl sulfides with broad functionalities was synthesized in good yields at room temperature. The present methodology is also applicable to benzo[d]thiazole-2-thiols, benzo[d]oxazole-2-thiol, 1H-benzo[d]imidazole-2-thiols, and 1H-imidazole-2-thiol.

A method for synthesis of aryl thioether compound

The invention discloses a synthetic method of an aryl thioether compound as shown in a formula (3). The polysubstituted aryl thioether compound is obtained by using aryl iodide or an aryl trifluoromethane sulphonate derivative and halogenated hydrocarbon as reaction raw materials and Na2S2O3 as a vulcanization reagent and reacting in a reaction solvent under the effect of a metal palladium catalyst. The synthetic method is mild in reaction conditions, simple in reaction operation and relatively high in productivity, can provide key skeleton structures for synthesis of lots of natural products and medicines and can be widely applied to industrialization scale production.

Thioetherification via Photoredox/Nickel Dual Catalysis

Hypervalent alkylsilicates represent new and readily accessible precursors for the generation of alkyl radicals under photoredox conditions. Alkyl radicals generated from such silicates serve as effective hydrogen atom abstractors from thiols, furnishing thiyl radicals. The reactive sulfur species generated in this manner can be funneled into a nickel-mediated cross-coupling cycle employing aromatic bromides to furnish thioethers. The serendipitous discovery of this reaction and its utilization for the thioetherification of various aryl and heteroaryl bromides with a diverse array of thiols is described. The S-H selective H atom abstraction event enables a wide range of functional groups, including those bearing protic moieties, to be tolerated. (Chemical Equation Presented).

An efficient iron-catalyzed S-arylation of aryl and alkylthiols with aryl halides in the presence of water under aerobic conditions

Abstract In this study, an environmentally benign FeCl3·6H2O/l-proline catalytic system in the presence of TBAB was employed as a catalyst for the coupling reactions of aryl halides with aryl and alkyl thiols in water under aerobic conditions. The versatility, low cost, and environmental friendliness, in combination with high yields, makes the procedure noteworthy. This protocol offers a simple and efficient thioetherification method for aryl halides.

Direct cross-coupling access to diverse aromatic sulfide: Palladium-catalyzed double C-S bond construction using Na2S 2O3 as a sulfurating reagent

The Pd-catalyzed cross-coupling of aryl halides, alkyl halides, and Na 2S2O3·5H2O to deliver aromatic thioethers is described. Pyridine, furan, thiophene, benzofuran, benzoxazole, benzothiophene, benzothiazole, and pyrazine are all amenable to this protocol. The odorless and stable solid Na2S2O 3·5H2O was used as a convenient and environmentally friendly source of sulfur. Pd-catalyzed cross-couplings without thiols or thiophenols to build C-S bonds have not previously been achieved, which renders our observation more striking.

Cu-catalyzed coupling of aryl iodides with thiols using carbonyl-phosphine oxide ligands

A series of carbonyl-phosphine oxide ligands were synthesized from 2-bromophenylaldehyde and used in Cu-catalyzed C-S coupling reactions. Aryl iodide and aryl bromide reacted with thiols efficiently upon catalysis under mild reaction conditions and a yiel

Cu-Catalyzed Coupling of Aryl Iodides with Thiols Using Carbonyl-Phosphine Oxide Ligands

A series of carbonyl-phosphine oxide ligands were synthesized from 2-bromophenylaldehyde and used in Cu-catalyzed C-S coupling reactions. Aryl iodide and aryl bromide reacted with thiols efficiently upon catalysis under mild reaction conditions and a yiel

Zinc-mediated palladium-catalyzed formation of carbon-sulfur bonds

(Chemical Equation Presented) A catalytic amount of zinc chloride in combination with a palladium catalyst ligated by a monodentate phosphine allows the coupling of aryl and alkyl thiols with aryl bromides in high yields. The addition of zinc chloride to a palladium catalyst system that reportedly failed to promote sulfide formation allows this once ineffective catalyst system to provide the sulfide product in good yield. This paper describes a high-yielding and general monodentate phosphine-ligated palladium catalyst for biaryl and alkyl aryl sulfide formation.