340169-30-4

Upstream product

• 56366-45-1 2-methyl-3-phenylthioindole 
• 74-88-4 methyl iodide 
• 875-79-6 1,2-dimethylindole 
• 194720-38-2 2,3,5,6-tetramethyl-4-oxo-1-phenylthiocyclohexa-2,5-dienyl 2-chloroacetate 
• 14204-27-4 N-phenylthiophthalimide 
• 882-33-7 diphenyldisulfane 
• 95-20-5 2-methyl-1H-indole 
• 77-78-1 dimethyl sulfate 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 169216-70-0 4-Benzenesulfinyl-2,3,5,6-tetramethyl-phenol 

Downstream Products

• 875-79-6 1,2-dimethylindole 

Relevant academic research and scientific papers

S-Aryl Arenesulfonothioate and Copper Acetate Mediated Arylthiolation of 2-Arylpyridines and Heteroarenes

Copper acetate mediated regioselective ortho-arylthiolation of 2-arylpyridines has been accomplished for the first time using S-aryl arenesulfonothioate as the arylthiolating agent. The reaction shows good functional group tolerance and gives thioarylated products in 67-89% yields. This reagent is a good alternative to unpleasant smelling arylthiols. Experimental evidence suggests an unprecedented insertion of an arylthio unit from both parts of the reagent (SPh and p-TolSO2) in the presence of copper acetate. Indoles and imidazopyridines also undergo facile reaction at the C-3 position and furnish thioarylated derivatives in good yields.

Indium chloride: A versatile Lewis acid catalyst for the synthesis of 3-sulfenylindoles

Indium chloride has been used as a versatile Lewis acid catalyst for the synthesis of 3-sulfenylindoles in good yields by the independent reaction of indoles and N-alkylindoles with N-(phenylthio)phthalimide in dimethyl formamide (DMF) at 100°C for about 5-6 h.

An efficient and clean CuI-catalyzed chalcogenylation of aromatic azaheterocycles with dichalcogenides

A highly efficient and environmentally friendly method for catalytic chalcogenylation of imidazopyridines, imidazopyrimidines, indoles, and pyrrolo[2,3-b]pyridines with dichalcogenides has been developed by using CuI as catalyst under air. The reactions proceed smoothly to give the desired products in moderate to excellent yields, without the presence of other additive.

Development of a novel, highly efficient halide-catalyzed sulfenylation of indoles

The reaction of a variety of indoles with N-thioalkyl- and N-thioarylphthalimides to produce 3-thioindoles is reported. Catalytic quantities of halide-containing salts are crucial to the success of this reaction. This highly efficient reaction provides sulfenylated indoles from bench-stable, readily available starting materials in good to excellent yields.

Facile and efficient sulfenylation method using quinone mono-O,S-acetals under mild conditions

A novel sulfenylation method induced by aromatization of quinone mono-O,S-acetals is described. These sulfenylation reagents readily react with silyl enolethers or electron rich aromatic compounds to give sulfenylation products under mild conditions. In particular, O,S-acetal 2j, which possesses a pentafluorophenylthio function, is the most effective reagent from the standpoint of the adaptability for various substrates.

Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides

Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction.We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring.In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched.Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides.This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.