647024-85-9

Upstream product

• 431878-80-7 2,3-bis[(4-methylphenyl)thio]-1H-indole 
• 741686-92-0 2-[(S_s)-(p-tolylsulfinyl)]indole 
• 40899-71-6 1-benzenesulfonylindole 
• 120-72-9 indole 
• 39549-10-5 1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione 
• 106-45-6 para-thiocresol 
• 624-31-7 4-tolyl iodide 
• 496-30-0 indolin-2-thione 
• 103-19-5 di(p-tolyl) disulfide 
• 933-00-6 p-methylbenzenesulfenyl chloride 
• 741686-91-9 1-benzenesulfonyl-2-[(S_s)-(p-tolylsulfinyl)]indole 
• 50444-99-0 (1R,2S,5R)-menthyl-(S)-p-toluenesulfinate 

Downstream Products

• 741686-94-2 1-crotonoyl-2-[(S_s)-(p-tolylsulfinyl)]indole 

Relevant academic research and scientific papers

Preparation method of 2-indole sulfide compounds

The invention provides a preparation method of 2-indole sulfide compounds. The method comprises the following steps: dissolving one indole compound, one sodium sulfinate compound and an accelerant into an organic solvent, performing stirring at a certain temperature until the reaction is completed, adding saturated brine into the obtained reaction solution, performing separation extraction on the organic phase, performing rotary evaporation dryness on an organic layer, and performing column chromatography or recrystallization to obtain the product. The method provided by the invention has the characteristics of mild reaction conditions, no need of adding other metal catalysts, a simple synthetic process and simple operation.

Copper-catalyzed synthesis of 2-sulfenylindoles from indoline-2-thiones and aryl iodides

A novel and efficient method for synthesis of 2-sulfenylindole via copper-catalyzed coupling reaction of indoline-2-thiones with aryl iodides has been developed. A series of N-substituted and N-free 2-sulfenylindole were obtained in high yields. Furthermo

TFA-promoted direct C-H sulfenylation at the C2 position of non-protected indoles

A simple, efficient and practical metal-free C-H sulfenylation process at the C2 position of non-protected indoles has been developed. 2-Thioindoles were obtained in moderate to high yields using stable and readily available N-(thio)succinimides at room temperature in the presence of TFA.

Synthesis of chiral sulfinyl-substituted 1-indolyl enones and asymmetric conjugate addition by an arylcopper reagent

The asymmetric conjugate addition of arylcopper reagents to chiral 1-[2-(p-tolylsulfinyl)]indolyl and 1-[3-(p-tolylsulfinyl)]indolyl enones was examined. With the 2-sulfinyl-indolyl derivatives, the reaction of the arylcopper reagent gave high diastereoselectivities (81-88% de's) to afford the adducts in excellent yields, although the similar addition reaction of the 3-sulfinyl derivatives afforded poor diastereoselectivities.

Mechanism of the second sulfenylation of indole

Sulfenylation of indole using a sulfenyl chloride occurs initially at the 3-position of the ring, leading to a 3-indolyl sulfide. When an excess of sulfenyl chloride is used, a second sulfide group is introduced at the 2-position, and an indolyl 2,3-bis-sulfide results. We have demonstrated that this second sulfenylation occurs not by direct introduction of the second sulfide at the 2-position but via initial formation of an indolenium 3,3-bis-sulfide intermediate, followed by migration of one of the sulfide groups to the 2-position. This was achieved by the isolation of two examples of 3H-indole 3,3-bis-sulfides and by subsequent demonstration that they rearrange to the indolyl 2,3-bis-sulfides by treatment with sulfenyl halides.