340169-29-1

Upstream product

• 1006-94-6 5-methoxylindole 
• 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 
• 1260119-61-6 5-methoxy-3-(diphenylsulfonio)indolide 
• 80-17-1 benzenesufonyl hydrazide 
• 618-41-7 Benzenesulfinic acid 
• 64605-34-1 1-(2-amino-5-methoxyphenyl)-2-chloroethan-1-one 
• 104-94-9 4-methoxy-aniline 
• 98-09-9 benzenesulfonyl chloride 
• 1859-03-6 ethyl benzenesulfinate 
• 873-55-2 sodium benzenesulfonate 
• 108-98-5 thiophenol 
• 128070-50-8 2-(phenyldisulfanyl)benzo[d]thiazole 

Downstream Products

• 633291-87-9 5-methoxy-3-(phenylsulfonyl)-1H-indole 

Relevant academic research and scientific papers

Palladium-Catalyzed Direct C2-Biarylation of Indoles

Biaryl and indole units are important structural motifs in several bioactive molecules and functional materials. We have accomplished straightforward access to C2-biarylated indole derivatives through palladium-catalyzed C-H activation strategy with a bro

NH4I/1,10-phenanthroline catalyzed direct sulfenylation of N-heteroarenes with ethyl arylsulfinates

An efficient synthesis of N-heterocyclic aryl sulfides via NH4I/1,10-phenanthroline-catalyzed direct sulfenylation reactions was reported. In this reaction, heteroarenes such as indoles, and pyrroles serve as nucleophiles by installing a arylthio group at the C3 and C2 position of heterocycles, respectively. With readily accessible and free of unpleasant odor ethyl arylsulfinates as sulfur reagents, the metal-free-catalyzed direct sulfenylation of N-heteroarenes has been developed. 3-Arylthio-indoles and 2-arylthio-pyrroles derivatives were obtained in moderate to excellent yields, even on gram scale. The reaction was general for a broad scope of substrates and demonstrated good tolerance to a variety of functional groups.

Synergistic Dual Role of [hmim]Br-ArSO2Cl in Cascade Sulfenylation-Halogenation of Indole: Mechanistic Insight into Regioselective C-S and C-S/C-X (X = Cl and Br) Bond Formation in One Pot

Bifunctionalized indoles are an important class of biologically active heterocyclic compounds and potential drug candidates. Because of the lack of efficient synthetic methods, one pot cascade synthesis of these compounds is rare and remains a challenge.

An electrochemical synthesized by catalytic oxidation of 3 - mercapto indole compounds

The invention discloses a synthesizing method for a 3-mercapto indole compound through electrochemical catalytic oxidation. According to the method, a three-electrode system is used, a cathode and ananode are graphite electrodes, and a silver nitrate acetonitrile solution of 0.1mol/L is used as a reference electrode; and the indole compounds, disulfide and potassium iodide are added in a sodium tetrafluoroborate acetonitrile solution, stirring and electrolytic reaction are conducted for 3-24h under the condition of the temperature of 45-75 DEG C and 0.2-0.6 V constant voltage, a reaction solution is post-processed, and the product 3-mercapto indole compound is obtained. By means of the synthesizing method, operation is simple, convenient and safe, the yield of the product 3-mercapto indole compound is high, the reaction condition is mild, clean electrical energy is used as a redox agent, and the environmental cost is greatly reduced.

Synergistic Cooperative Effect of Sodium borohydride-Iodine Towards Cascade C?N and C?S/Se Bond Formation: One-pot Regioselective Synthesis of 3-Sulfenyl/selenyl Indoles and Mechanistic Insight

In this work, a new strategy to synthesize 3-sulfenyl/selenyl indole is reported wherein LC?MS reveals a novel insight into synergistic cooperative effect of NaBH4-I2 which allows cascade C?N and C?S/C?Se bond formations via reduction-nucleophilic cyclization-chalcogenylation, three steps in one-pot, towards regioselective synthesis of diverse 3-chalcogenyl indoles including 5-bromo-3-[(3,4,5-trimethoxyphenyl)thio]-1H-indole, a known lead anticancer compound, directly from 2-amino-phenacylchlorides and thiophenols or disulfides/diselenides in aqueous dioxane under transition-metal-free condition. (Figure presented.).

Metal Free Mono- and 2,3-Bis-sulfenylation of Indoles in Water with Sodium Sulfinates as a Sulfur Source

An iodine-PPh3 mediated sulfenylation of indoles in water with stable and odorless sodium sulfinates as the sulfur source is described. The reaction could afford monosulfenylated indoles in moderate to excellent yields under metal free conditions. Moreover, double C—H sulfenylation of indoles at 2- and 3-positions has also been achieved by using excess sodium sulfinates under the optimized reaction conditions.

Electrochemical sulfenylation of indoles with disulfides mediated by potassium iodide

A novel electrochemical system for sulfenylation of indoles with disulfides to generate 3-sulfenylindoles via C-S bond formation mediated by potassium iodide at a low potential was developed. Iodine was electrogenerated from iodide ions at a graphite anode and showed a high catalytic activity for the electrochemical sulfenylation reactions. A variety of aromatic, heteroaromatic and aliphatic disulfides could react with 2-methlyindole to synthesize the corresponding 3-sulfenylindoles in good to excellent yields. In addition, protected and unprotected indoles with various groups, especially electron-donating groups, also performed well in the sulfenylation reactions. The transformation, which proceeded through the redox of iodine and the generation of intermediate 3-iodoindole, provided an efficient and environmentally benign protocol for the synthesis of 3-sulfenylindoles under mild conditions.

An efficient: T -BuOK promoted C3-chalcogenylation of indoles with dichalcogenides

A versatile and efficient method for the synthesis of 3-chalcogenyl-indoles from indoles and dichalcogenides employing t-BuOK as a promoter at room temperature has been achieved. The present protocol exhibited a broad functional group tolerance. Diverse 3-sulfenyl- and 3-selenyl-indoles were rapidly obtained in good to excellent yields with high regioselectivities. It is noteworthy that this transformation was applicable to N-protected and N-unprotected indoles, allowing N-deprotection and C3-chalcogenylation of indoles in one step.

Direct, Metal-free C(sp2)?H Chalcogenation of Indoles and Imidazopyridines with Dichalcogenides Catalysed by KIO3

Herein, we report a greener protocol for the synthesis of 3-Se/S-indoles and imidazo[1,2-a]pyridines through direct C(sp2)?H bond chalcogenation of heteroarenes with half molar equivalents of different dichalcogenides, using KIO3 as a non-toxic, easy-to-handle catalyst and a stoichiometric amount of glycerol. The reaction features are high yields, based on atom economy, easy performance on gram-scale, metal- and solvent-free conditions as well as applicability to different types of N-heteroarenes.

Iodine-Catalyzed Mono- and Disulfenylation of Indoles in PEG400 through a Facile Microwave-Assisted Process

An iodine-catalyzed versatile and green method for the synthesis of mono- and 2,3-disulfenylindoles was developed. Various indoles reacted with sodium alkyl- and arylsulfinates by using hydrogen peroxide as the oxidizing agent in PEG400 under microwave conditions. This simple method enabled the rapid synthesis of mono- and 2,3-disulfenylindoles in good to excellent yields under metal-free conditions. Furthermore, this protocol is environmentally friendly, odorless, and operationally easy and can be performed within short reaction times under mild reaction conditions with excellent functional-group tolerance.