112425-44-2

Upstream product

• 21954-69-8 diethyl-amidosulfurous acid methyl ester 
• 6674-22-2 1,8-diazabicyclo[5.4.0]undec-7-ene 
• 670-98-4 methyl benzenesulfinate 
• 109-89-7 diethylamine 
• 6667-19-2 benzenenesulfenyl dimethylamine 
• 882-33-7 diphenyldisulfane 
• 108-98-5 thiophenol 
• 38078-09-0 diethylamino-sulfur trifluoride 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 98-80-6 phenylboronic acid 
• 1192-40-1 copper(I) thiophenolate 
• 934-87-2 S-phenyl thioacetate 
• 873-55-2 sodium benzenesulfonate 
• 4972-29-6 benzenesulphinyl chloride 

Downstream Products

• 1709-50-8 N,N-diethylbenzenesulfonamide 

Relevant academic research and scientific papers

Improved synthesis of 1-benzenesulfinyl piperidine and analogs for the activation of thioglycosides in conjunction with trifluoromethanesulfonic anhydride

An improved protocol for the large-scale production of 1-benzenesulfinyl piperidine and other sulfinamides is described. It is demonstrated that 1-benzenesulfinyl pyrrolidine and N,N-diethyl benzenesulfinamide function analogously to 1-benzenesulfinyl pip

Highly Chemoselective NH- and O-Transfer to Thiols Using Hypervalent Iodine Reagents: Synthesis of Sulfonimidates and Sulfonamides

Aryl thiols can be selectively converted to sulfonimidates or sulfonamides with three new S-X connections being made selectively in one pot. Using hypervalent iodine reagents in the presence of ammonium carbamate, NH- and O-groups are transferred under mild and practical conditions. Reducing the loading of ammonium carbamate changed the product distribution, converting the sulfonimidate to the sulfonamide. Studies into the possible intermediate species are presented, suggesting that multiple pathways may be possible via sulfinate esters, or related intermediates, with each species forming the same products.

A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides

Unprotected tertiary sulfonimidamides have been prepared in good to excellent yields in a one-pot transformation from tertiary sulfinamides through NH transfer. The reaction is mediated by commercially available (diacetoxyiodo)benzene and ammonium carbamate in methanol under convenient conditions. A wide range of functional groups are tolerated and initial results indicate that the NH transfer is stereospecific. A small molecule X-ray analysis of NH sulfonimidamide 2 a and its behavior in selected in vitro assays in comparison to the matched sulfonamide are also reported. This new reaction provides a safe, short and efficient approach to sulfonimidamides, which have been the subject of recent, growing interest in the life sciences.

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

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

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.

A new method for oxidation of various alcohols to the corresponding carbonyl compounds by using n-t-butylbenzenesulfinimidoyl chloride

Various primary and secondary alcohols were smoothly oxidized to the corresponding aldehydes and ketones by using a new oxidizing agent, N-t-butylbenzenesulfinimidoyl chloride (4a), in the coexistence of DBU or zinc oxide. The present oxidation proceeded under mild conditions via five-membered intramolecular proton-transfer of an alkyl arenesulfinimidate intermediate.

REACTION OF DIMETHYL SULFITE WITH PHENYLLITHIUM. FORMATION OF BIPHENYL AND DIPHENYL SULFIDE VIA SULFURANE

Dimethyl sulfite reacted an excess of phenyllithium yielding biphenyl and diphenyl sulfide in good yield.Other dialkyl sulfites also reacted giving identical yields of biphenyl and diphenyl sulfide irrespective of the structure of the aryl groups, indicating that dialkyl sulfites can be used for the reaction with aryllithiums in place of diaryl sulfoxides.The mechanism of the reaction of diaryl sulfoxides with aryllithium is discussed on the the basis of the isomer distribution of bitolyls, the effect of additives, and the ratio of the benzyne and sulfonium salt pathways.Sulfurane 1 is formed in an initial stage of the reaction of diaryl sulfoxide with aryllithium followed by its competitive collapse by way of benzyne and sulfonium salt pathways.