182356-71-4

Upstream product

• 123-75-1 pyrrolidine 
• 931-59-9 benzenesulfenyl chloride 
• 670-98-4 methyl benzenesulfinate 
• 882-33-7 diphenyldisulfane 
• 618-41-7 Benzenesulfinic acid 
• 108-98-5 thiophenol 
• 873-55-2 sodium benzenesulfonate 
• 4972-29-6 benzenesulphinyl chloride 

Downstream Products

• 5033-22-7 1-(phenylsulfonyl)-pyrrolidine 

Relevant academic research and scientific papers

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.

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.

A Selectfluor-promoted oxidative reaction of disulfides and amines: access to sulfinamides

An unprecedented transition-metal-free oxidative reaction of disulfides and amines with Selectfluor as a mild oxidant under aerobic conditions was developed. This reaction was conducted under mild conditions and tolerated a wide range of coupling partners including disulfides and amines, affording the corresponding sulfinamide products in good chemical yields. Furthermore, this reaction could be used in gram-scale synthesis. This reaction enriches the research content of Selectfluor and provides a valuable vista for the convenient synthesis of sulfinamides.

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.

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.

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

Selective Alkylation of β-Ketoester Enolates using O-Methyl Aminosulfoxonium salts; the First Example of C-alkylation using Sulfoxonium Salt Electrophiles

The alkylation of β-ketoester enolates with O-methyl aminosulfoxonium tetraphenylborate salts is reported; good to excellent selectivity for C- vs.O-alkylation is observed, and is found to be dependent on the nature of the β-ketoester, solvent, metal counterion and aminosulfoxonium salt.