6873-90-1

Upstream product

• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 100-46-9 benzylamine 
• 536-57-2 p-toluene sulfinic acid 
• 672-78-6 methyl p-toluene sulfinate 
• 98-59-9 p-toluenesulfonyl chloride 
• 6873-55-8 p-tolylsulfinyl amide 
• 1365659-60-4 C₁₄H₁₅NS 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 1858-86-2 Ethyl p-toluenesulfinate 

Downstream Products

• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 31536-19-3 allyl 4-methylbenzenesulfinate 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 1020731-54-7 N-benzyl-N-diphenylphosphanyl-p-tolylsulfinamide borane 
• 102-97-6 Benzyl-isopropyl-amin 
• 780-25-6 N-benzylidene benzylamine 
• 100-52-7 benzaldehyde 
• 1351958-49-0 (Rs)-N-benzyl-4-methylbenzenesulfinamide 
• 169330-83-0 (S)-N-benzyl-4-methylbenzenesulfinamide 
• 93938-07-9 N-benzyl-p-toluenesulfonimidomorpholide 
• 138711-78-1 C₁₉H₂₃NOS 
• 138711-66-7 C₁₇H₁₉NOS 
• 123552-96-5 C₁₆H₁₉NOS 
• 103-67-3 benzyl-methyl-amine 

Relevant academic research and scientific papers

Synthetic preparation of N-alkyl and N-aryl arenesulfinamides using an arenesulfinic acid-CDI driven approach

A new synthetic methodology has been developed for the synthesis of N-alkyl and N-aryl arenesulfinamides. The methodology involved reacting arenesulfinic acids (R = -Me, -H, -Cl) with 1,1’-carbonyldiimidazole (CDI) to form the reactive intermediate, an arenesulfinylimidazole. This intermediate was then reacted with both primary and secondary amines to yield the corresponding N-alkyl sulfinamides in yields up to 90%. While the overall yields ranged from 52% to 90%, the level of diastereoselection with racemic or enantiomerically enriched amines only reached a level of 54:46 favoring the major diastereomer as determined by analysis of the 500 MHz 1H NMR spectra. A series of aniline derivatives were also investigated as coupling partners and were found to form the N-aryl arenesulfinamide in good yield.

Rare-Earth-Catalyzed Transsulfinamidation of Sulfinamides with Amines

A rare-earth-catalyzed transsulfinamidation of primary sulfinamides with alkyl, aryl, and heterocyclic amines for the synthesis of diverse secondary and tertiary sulfinamides has been realized. Unlike transition metal-catalyzed cross-coupling approaches restricted to non-commercially available disubstituted O-benzoyl hydroxylamines, this newly developed protocol is suitable for diverse readily available primary and secondary amines without any modifications. Excellent catalytic activity and selectivity are achieved with Eu(OTf)3 under mild reaction conditions, which extends the applicability of rare-earth catalysis.

Kinetic Resolution of Sulfinamides via Asymmetric N-Allylic Alkylation

An efficient kinetic resolution of sulfinamides via an asymmetric N-allylic alkylation reaction was realized using hydroquinine as a catalyst under mild conditions. The kinetic resolution of a range of Morita-Baylis-Hillman adducts and N-aryl tert-butylsulfinamides was highly effective. In addition, the synthetic utility of the protocol was demonstrated by a scaled-up reaction. Density functional theory calculations provide convincing evidence for the interpretation of stereoselection.

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

Ni/NHC-catalyzed cross-coupling of methyl sulfinates and amines for direct access to sulfinamides

It was reported to develop a simple and convenient method for the Ni/NHC-catalyzed cross-coupling of methyl sulfinates and amines without an acid/base to afford secondary or tertiary sulfinamides in moderate to good yields. The method can provide the desired products with broad substrate scope, good chemoselectivity and good functional group compatibility. The presented approach may enrich the Ni/NHC catalyst system and promote the applications of methyl sulfinates in the organic sulfur chemistry.

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.

Efficient Synthesis of Sulfinate Esters and Sulfinamides via Activated Esters of p -Toluenesulfinic Acid

Sulfinate esters were prepared by the process of activating p -toluenesulfinic acid with either cyanuric chloride, methanesulfonyl chloride, or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC-HCl). Activation of p -toluenesulfinic acid with cyanuric chloride led to the formation of sulfinate esters that were accompanied by the formation of the corresponding sulfones. The use of methanesulfonyl chloride for activation via methanesulfonic p -toluenesulfinic anhydride afforded mixtures of sulfinate esters and methanesulfonates. The use of the carbodiimide EDC proved to yield the best results with the highly selective formation of the target sulfinate esters. The use of trimethylacetic p -toluenesulfinic anhydride or cyanuric chloride to achieve the synthesis of sulfinamides proved to be ineffective due to poor chemoselectivity of the nucleophilic attack on the activated p -toluenesulfinic acid anhydride. Ultimately, the use of EDC-HCl to form the sulfinamides proved to be the best pathway for synthesis.

Fast and efficient synthesis of sulfinamides by the oxidation of sulfenamides using potassium fluoride and m-chloroperoxybenzoic acid

A procedure for the synthesis of N-alkyl-, N-cycloalkyl-, N,N-dialkyl-, and N-arylarenesulfinamides from the corresponding sulfenamides using KF/m-chloroperoxybenzoic acid (CPBA) in CH3CN-H2O is described. High efficiency (fast react

Monoalkylation of primary amines and N-sulfinylamides

An efficient monoalkylation of primary amines with primary or secondary alcohols catalyzed by Ra-Ni under mild conditions is described. The Royal Society of Chemistry.

N-phosphino-p-tolylsulfinamide ligands: Synthesis, stability, and application to the intermolecular Pauson-Khand reaction

(Chemical Equation Presented) Here we synthesized a family of racemic and optically pure N-phosphino-p-tolylsulfinamide (PNSO) ligands. Their stability and coordination behavior toward dicobalt-alkyne complexes was evaluated. Selectivities of up to 3:1 we