6829-66-9

Upstream product

• 21230-20-6 benzenesulfinyl azide 
• 109-73-9 N-butylamine 
• 23837-25-4 N-(phenylthio)-N-(normal-butyl)amine 
• 71-43-2 benzene 
• 873-55-2 sodium benzenesulfonate 
• 4972-29-6 benzenesulphinyl chloride 
• 98-88-4 benzoyl chloride 
• 670-98-4 methyl benzenesulfinate 

Downstream Products

• 3622-84-2 N-butylbenzenesulfonamide 
• 75421-81-7 2-(benzenesufinyl)-1-methyl-1H-pyrrole 
• 108698-57-3 1-methyl-3-(phenylsulfinyl)-1H-indole 
• 75421-90-8 1-methyl-3-(phenylsulfinyl)-1H-pyrrole 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 1197-26-8 S-phenyl benzenesulfonothioate 

Relevant academic research and scientific papers

Direct conversion of sulfinamides to thiosulfonates without the use of additional redox agents under metal-free conditions

Direct conversion of sulfinamides to thiosulfonates is described. Without the use of additional redox agents, the reaction proceeds smoothly in the presence of TFA under metal-free conditions. This protocol possesses many advantages such as odourless and stable starting materials, broad substrate scope, selective synthesis, and mild reaction conditions. This journal is

Regioselective and oxidant-free sulfinylation of indoles and pyrroles with sulfinamides

An unexpected time-controlled highly selective C3-or C2-sulfinylation of pyrroles with sulfinamides is reported for the first time. The sulfinylation of indoles with sulfinamides using this protocol is oxidant-free and can be performed under obviously more feasible conditions (1.2 equiv. of indoles, 10 min) in comparison with the precedent procedure (3-20 equiv. of indoles, 16-18 h, ammonium persulfate as oxidant, hv). A variety of functional groups were tolerated, and various C2-thioindoles and C2/3-thiopyrroles were obtained in moderate to excellent yields.

Visible-Light-Accelerated C?H Sulfinylation of Heteroarenes

Heteroaromatic sulfoxides are a frequent structural motif in natural products, drugs, catalysts, and materials. We report a metal-free visible-light-accelerated synthesis of heteroaromatic sulfoxides from sulfinamides and peroxodisulfate. The reaction proceeds at room temperature with blue-light irradiation and allows the C?H sulfinylation of electron-rich heteroarenes, such as pyrroles and indoles. An electrophilic aromatic substitution mechanism is proposed based on the substrate scope, substitution selectivity, and competition experiments with different nucleophiles.

One-pot synthesis of sulfonamides from methyl sulfinates using ultrasound

Room temperature ultrasonic irradiation of neat mixtures of methyl sulfinates and primary or secondary amines (1.5 equiv) produced sulfinamides, which on m-CPBA oxidation (in dichloromethane) were converted into the corresponding sulfonamides. The two steps can be accomplished in one pot, in good overall yields, when using secondary amines, but primary amines give better sulfonamide yields when the peracid oxidation is effected on the purified sulfinamide. This constitutes a mild, efficient, and potentially scalable route to sulfonamides, which obviates the use of water sensitive, often lachrymatory sulfonyl chlorides and large reagent excesses.

Experimental and Computational Evidence for the Formation of Iminopersulfinic Acids

An experimental and computational study of the reactions of singlet oxygen with N-substituted sulfenamides is reported. Intermediates capable of epoxidizing norbornene were observed during the photooxidations of three sulfenamides. These results are used to argue for formation of iminopersulfinic acids. The structural integrity of two iminopersulfinic acids was supported by their successful location at the MP2/6-31G* level of theory. Furthermore, the inability to locate computationally significant persulfinimide precursors suggests that the iminopersulfinic acids form by enelike reactions involving near-simultaneous addition of singlet oxygen to sulfur and hydrogen abstraction.

Reaction of Benzenesulfinyl Azide with Thiols and Amines. Preparation of Thiosulfinates and Sulfinamides

Reaction of benzenesulfinyl azide (1) with thiols at -20 deg C gave thiosulfinates and hydrazoic acid.Reaction of 1 with primary and secondary amines gave sulfinamides and hydrazoic acid.The presence of a hydroxyl group in the thiol or amine did not change the course of the reaction.Thus, a thiosulfinate and sulfinamide containing a free hydroxyl group could be prepared.Yields ranging from 41percent to 93percent were obtained.