26652-46-0

Upstream product

• 896-80-0 1-benzenesulfonyl-2,4-dinitro-benzene 
• 67-64-1 acetone 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 151-50-8 potassium cyanide 
• 27846-25-9 1-phenyl-2-(phenylsulfonyl)ethane 
• 67100-45-2 4-benzenesulfonyl-5-phenyl-1-pentene 
• 124992-97-8 2-(1,3-diphenylpropyl) phenyl sulfone 
• 124993-02-8 2-benzyl-1,3-diphenylpropyl phenyl sulfone 
• 13909-34-7 N-benzylidenephenylsulfonamide 
• 98-10-2 benzenesulfonamide 
• 127-63-9 diphenyl sulphone 
• 3112-85-4 methylphenylsulfonate 

Downstream Products

• 144888-18-6 2-(phenylsulfonyl)-1-(thiophen-2-yl)ethan-1-one 
• 1174712-62-9 3-(phenyl(phenylsulfonyl)methyl)-1H-indole 

Relevant academic research and scientific papers

Late-Stage 18O Labeling of Primary Sulfonamides via a Degradation–Reconstruction Pathway

A late-stage 18O labeling approach of sulfonamides that employs the corresponding unlabeled molecule as the starting material was developed. Upon deamination of the sulfonamide, a sulfinate intermediate was isotopically enriched using eco-friendly reagents H218O and 15NH3(aq) to afford a M+5 isotopologue of the parent compound. This degradation–reconstruction approach afforded isolated yields of up to 96 % for the stable isotope labeled (SIL) sulfonamides, and was compatible with multiple marketed therapeutics, including celecoxib, on a gram scale. The SIL products also exhibited no 18O/16O back exchange under extreme conditions, further validating the utility of this green strategy for drug labeling for both in vitro and in vivo use. This procedure was also adapted to include pharmaceutically relevant methyl sulfones by using 13CH3, affording M+5 isotopic enrichment, thereby illustrating the broad utility of this methodology.

NHC-Catalyzed Deamination of Primary Sulfonamides: A Platform for Late-Stage Functionalization

Herein we describe the development and application of a method for the mild, late-stage conversion of primary sulfonamides to several other other functional groups. These reactions occur via initial reductive deamination of sulfonamides to sulfinates via an NHC-catalyzed reaction of transiently formed N-sulfonylimines. The method described here is tolerant of nearly all common functional groups, as exemplified by the late-stage derivatization of several complex pharmaceutical compounds. On the basis of the prevalence of sulfonamide-containing drugs and building blocks, we have developed a method to enable sulfonamides to be applied as versatile synthetic handles for synthetic chemsitry.

Aromatization modulates the activity of small organic molecules as promoters for carbon-halogen bond activation

The combination of small organic molecules and a base serves as a unique system for the activation carbon-halogen bonds in haloarenes by single electron transfer (SET). However, most of the molecules employed as promoters only allow for the activation of aryl iodides, and efficient activation of aryl bromides and chlorides under this mode is still rather challenging. Herein, we report the discovery of a structurally simple yet powerful promoter molecule, indoline, which exhibits unusually high activity in promoting the activation of haloarenes by SET. In the presence of t-BuOK and a trace amount of oxygen, indoline promotes the formation of aryl radicals not only from aryl iodides and bromides, but also from unactivated aryl chlorides (e.g., chlorobenzene) under relatively mild conditions. Mechanistic studies reveal the molecular basis for its high activity, for which the aromatization process plays a key role in modulating the electron transfer process.

Alkene synthesis: Elimination of arenesulfinic acid from alkyl aryl sulfones using potassium trimethylsilanolate as base

The use of potassium trimethylsilanolate as base to induce elimination of potassium arenesulfinate from alkyl aryl sulfones to produce E-alkenes is described. The reaction was appropriate for substrates containing a benzyl or allyl group α to the sulfone

A new preparative method of thiocanates by the solid state thiosulfonate/cyanide reaction

The mixing and heating of thiosulfonates with potassium cyanide in the solid state gave a variety of thiocyanates in good yield. This method provides easy access to aryl thiocyanates.

Preparation of polyenes

An improved process for the preparation of polyenes by the Julia reaction comprises carrying out the allylation of the anion of an allyl aryl sulfone generated a strong base, and the elimination of arylsulfinic acid to form a double bond in the same inert polar solvent which is immiscible with water, preferably in a ketone of the formula I where R1 and R2 are each straight-chain or branched alkyl of 2 to 4 carbons, or R1 and R2 together are tetramethylene or pentamethylene. The process is particularly important for the preparation of vitamin A derivatives. In the preparation of vitamin A aldehyde, for example, it is advantageous to use the same alkali metal alcoholate as strong base in both stages so that the conversion can be carried out as one-pot reaction.

REACTIONS OF AROMATIC NITRO COMPOUNDS. LVI. REACTION OF POLYNITRODIPHENYL SULFONES WITH ACETONE AND POTASSIUM HYDROXIDE

The Yanovskii ? complexes of 2,4-dinitrophenyl sulfone and 2,4-dinitro-, 2,4,4'-trinitro-, and 2,2',4,4'-tetranitrodiphenylsulfones were obtained and isolated in the crystalline form.It was established by PMR, IR, and electronic spectroscopy that they are