21179-27-1

Upstream product

• 24398-14-9 1-[(diethylamino)sulfanyl]-4-methylbenzol 
• 6873-55-8 p-tolylsulfinyl amide 
• 109-89-7 diethylamine 
• 1517-82-4 (-)-menthyl p-toluenesulfinate 
• 61582-64-7 N,N-diethyl-O-benzoylhydroxylamine 
• 38078-09-0 diethylamino-sulfur trifluoride 
• 5720-05-8 4-methylphenylboronic acid 
• 195062-57-8 p-tolylboronic pinacol ester 
• 103-19-5 di(p-tolyl) disulfide 
• 106-45-6 para-thiocresol 
• 672-78-6 methyl p-toluene sulfinate 
• 98-59-9 p-toluenesulfonyl chloride 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 91378-37-9 S,S-diphenyl-(N-p-tolylfulfinyl)sulfoximine 

Downstream Products

• 649-15-0 N,N-diethyl-4-methylbenzenesulfonamide 
• 64396-66-3 methyl (R)-4-methylbenzenesulfinate 
• 59203-01-9 (S)-(+)-1-methyl 4-methylbenzenesulfinate 
• 112458-71-6 ethyl (R)-4-methylbenzenesulfinate 
• 59203-02-0 (R)-ethyl p-toluenesulfinate 
• 422509-92-0 4-Methyl-benzenesulfinic acid (S)-propyl ester 
• 70003-95-1 isopropyl (R)-4-methylbenzenesulfinate 
• 59203-03-1 (R)-isopropyl p-toluenesulfinate 
• 1858-86-2 Ethyl p-toluenesulfinate 

Relevant academic research and scientific papers

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.

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.

Copper-Catalyzed Transsulfinamidation of Sulfinamides as a Key Step in the Preparation of Sulfonamides and Sulfonimidamides

Secondary or tertiary sulfinamides are prepared by copper-catalyzed transsulfinamidation of primary sulfinamides with O-benzoyl hydroxylamines. Subsequent oxidations of the resulting products lead to the corresponding sulfonamides. Treatment of N-aryl sulfinamides with O-benzoyl hydroxylamines under copper catalysis provides N-aryl sulfonimidamides.

Metal-Free Cross-Coupling of Arylboronic Acids and Derivatives with DAST-Type Reagents for Direct Access to Diverse Aromatic Sulfinamides and Sulfonamides

We have developed a simple and convenient method for the cross-coupling of arylboronic acids and their derivatives with DAST-type reagents under mild and metal-free conditions to directly afford sulfinamides in moderate to good yields. Moreover, sulfonamides were obtained after a simple oxidation reaction. The reaction mechanism was investigated by18O-labeling experiments, and the synthetic utility was demonstrated by the sulfoxidation of natural products.

Copper-Catalyzed Oxidative Synthesis of Sulfinamides Using Thiols or Disulfides with Amines

Copper-catalyzed coupling of thiols with amines was used to synthesize numerous sulfinamides in excellent yields. Sulfenamides or sulfonamides were also formed as reaction byproducts albeit in trace quantities. The procedure is carried out as a one step a

Acid catalyzed alcoholysis of sulfinamides: Unusual stereochemistry, kinetics and a question of mechanism involving sulfurane intermediates and their pseudorotation

The synthesis of optically active sulfinic acid esters has been accomplished by the acid catalyzed alcoholysis of optically active sulfinamides. Sulfinates are formed in this reaction with a full or predominant inversion of configuration at chiral sulfur or with predominant retention of configuration. The steric course of the reaction depends mainly on the size of the dialkylamido group in the sulfinamides and of the alcohols used as nucleophilic reagents. It has been found that bulky reaction components preferentially form sulfinates with retention of configuration. It has been demonstrated that the stereochemical outcome of the reaction can be changed from inversion to retention and vice versa by adding inorganic salts to the acidic reaction medium. The unusual stereochemistry of this typical bimolecular nucleophilic substitution reaction, as confirmed by kinetic measurements, has been rationalized in terms of the addition-elimination mechanism, A-E, involving sulfuranes as intermediates which undergo pseudorotations.

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

The sulfinyl moiety in Lewis base-promoted allylations

By employing Senanayake's oxathiazolidine-2-oxide reagent, a collection of sulfinamides was prepared and provided the first examples of sulfinamides promoting the allylation of benzaldehyde and N-benzoylhydrazones with allyltrichlorosilane. The optimum su

Mild and general method for the synthesis of sulfonamides

Reaction of methyl sulfinates with lithium amides followed by 3-chloroperoxybenzoic acid oxidation of the resulting sulfinamides provides primary, secondary, and tertiary alkane-, arene-and heteroarenesulfonamides in high yields. This constitutes a mild and facile experimental protocol that avoids the use of hazardous, unstable, or volatile reagents and does not affect the configurational stability of the amines. Georg Thieme Verlag Stuttgart.

Expedient synthesis of sulfinamides from sulfonyl chlorides

Sulfinamides were synthesized from sulfonyl chlorides using a procedure involving in situ reduction of sulfonyl chlorides. The reaction is broad in scope and easy to perform.