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Upstream product

• 83-34-1 3-Methylindole 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 98-59-9 p-toluenesulfonyl chloride 
• 1858-86-2 Ethyl p-toluenesulfinate 
• 1593-60-8 p-toluenesulfonylhydroxylamine 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Relevant academic research and scientific papers

Catalyst-free sulfenylation of indoles with sulfinic esters in ethanol

A novel catalyst-free method for the synthesis of structurally diverse indole thioethers in moderate to excellent yields has been developed. In this reaction, sulfinic esters serve as new sulfur electrophiles.

Cu-catalysed direct bis-thiolation of benzoheterocycles with arylsulfonyl hydrazides

A series of bis-arylsulfenylated indoles (10), benzofurans (3), and benzothiophenes (3) and of monosulfenylated indoles (5), 12 of which are novel, were prepared in good yields via a Cu-catalysed direct sulfenylation of benzoheterocycles with arylsulfonyl hydrazides. Sulfonothioates are probably the major thiolated intermediates in this transformation.

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.

TBAI-mediated regioselective sulfenylation of indoles with sulfonyl chlorides in one pot

A versatile method for the synthesis of 3-sulfenylated indoles via TBAI promoted sulfenylation of indoles with sulfonyl chlorides in one pot has been presented. This system features highly regioselective, metal-free, easy operation, and shows a broad functional group tolerance leading to excellent yields. And this reaction could be easily conducted in 10 mmol scale with high effectivity. A plausible mechanism is proposed.

N-Hydroxy sulfonamides as new sulfenylating agents for the functionalization of aromatic compounds

An unprecedented use of N-hydroxy sulfonamides as sulfenylating agents has been established. In the presence of catalytic amounts of iodine and N-hydroxysuccinimide, N-hydroxy sulfonamides participated in sulfenylation with indoles, 7-azaindole, N-methyl pyrrole, and 2-naphthol to afford structurally diverse thioethers in moderate to excellent yields with very high regioselectivity.

Copper-catalyzed aerobic oxidative N-S bond functionalization for C-S bond formation: Regio- and stereoselective synthesis of sulfones and thioethers

A regio- and stereoselective synthesis of sulfones and thioethers by means of CuI-catalyzed aerobic oxidative N-S bond cleavage of sulfonyl hydrazides, followed by cross-coupling reactions with alkenes and aromatic compounds to form the C-sp-2-S bond, is described herein. N2 and H2O are the byproducts of this transformation, thus offering an environmentally benign process with a wide range of potential applications in organic synthesis and medicinal chemistry. First cleave, then cross-couple: A direct Cu-catalyzed aerobic oxidative C-sp-2-H functionalization and C-S bond coupling reaction has been developed (see scheme). By slight modification of the additive, sulfonyl hydrazides could serve as sulfonation, sulfenation, or arylation reagents to undergo cross-coupling reactions with alkenes and (hetero)aromatic cycles, affording sulfones, thioethers, and biaryl compounds with high regio- and stereoselectivities (see scheme).

Iodine-PPh3-mediated C3-sulfenylation of indoles with sodium sulfinates

3-(Alkylsulfanyl)- and 3-(arylsulfanyl)indoles were efficiently prepared by the reaction of indoles with sodium sulfinates mediated by iodine-PPh 3 in ethanol. The salient features of the present protocol are simplicity, high efficiency, non-anhydrous conditions, environmentally friendly reagents and solvent, and short reaction time.

K2S2O8/arenesulfinate: An unprecedented thiolating system enabling selective sulfenylation of indoles under metal-free conditions

An unprecedented thiolating system K2S2O8/arenesulfinate is described for selective sulfenylation of indoles in CH3CN/H2O. This metal-free strategy enables a simple, efficient and environment-benign approach to the pharmaceutically important candidates, 3-arylthioindoles. Catalytically reactive halogen and aryl groups are well tolerated. This journal is