142572-73-4

Upstream product

• 142572-60-9 Methyl-{1-[1-(toluene-4-sulfonyl)-meth-(Z)-ylidene]-pentyl}-amine 
• 693-02-7 hex-1-yne 
• 1070656-91-5 2-n-butyl-3-(p-toluenesulfonyl)-4,5,6,7-tetrahydro-3aH-isoxazolo[2,3-a]pyridine 
• 104-15-4 toluene-4-sulfonic acid 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 142321-29-7 1-(hex-1-en-2-yl)-1H-benzo[d][1,2,3]triazole 
• 68819-94-3 p-tolyl benzeneselenosulfonate 
• 108918-97-4 (E)-2-(phenylseleno)-1-(p-tolylsulfonyl)-1-hexene 

Relevant academic research and scientific papers

Method for efficiently synthesizing beta-ketone sulfonyl compounds through visible light induction

The invention provides a method for efficiently synthesizing beta-ketone sulfonyl compounds through visible light induction. The method specifically comprises steps as follows: in the presence of an organic solvent and at the room temperature, enol sulfonate compounds are taken as a raw material and react for 1-12 h through induction of visible light under the catalysis action of an organic compound serving as a photocatalyst, and the beta-ketone sulfonyl compounds are prepared. Compared with an existing method, the method has a wide applicable substrate range, a substrate is convenient and easy to obtain, reaction conditions are mild, operation is simple and convenient, the reaction efficiency is high, and the method has huge value in industrial application.

Photoinduced rearrangement of vinyl tosylates to β-ketosulfones

We developed a photoinduced radical fragmentation and rearrangement of vinyl tosylates that enables efficient formation of β-ketosulfones. This process is based on the photoinitiated homolysis of vinyl tosylate to release a sulfinyl radical from the tosyl group and the subsequent addition of a sulfinyl radical to another vinyl tosylate to form the desired β-ketosulfones. This simple protocol features a broad scope with both aromatic and aliphatic substrates, convenient reagents and operating systems.

Ambient benzotriazole ring opening through intermolecular radical addition to vinyltriazole

Radical addition to vinyltriazole was developed as a new approach to achieve 1,2,3-triazole ring opening under mild conditions. Through reagent control, excellent chemoselectivity was achieved, giving either nitrile under basic conditions or quinoxaline under neutral conditions. Reactivities made this method an attractive new reaction mode.

1,3-Dipolar cycloadditions of acetylenic sulfones in solution and on solid supports

(Chemical Equation Presented) Several representative acetylenic sulfones were immobilized on a polymer support derived from Merrifield resin by means of ester linkers that were used to couple free carboxylic acid groups on the solid support with benzylic hydroxyl functions on the arylsulfonyl moieties of the acetylenes. Several examples of reversed ester linkers, using Merrifield resin directly, were also successfully prepared. The 1,3-dipolar cycloadditions of the solid-supported acetylenic sulfones were investigated with a series of 1,3-dipoles, including benzyl azide, ethyl diazoacetate, diazomethane, as well as representative nitrile oxides, nitrile imines, nitrile ylides, nitrones, azomethine imines, azomethine ylides, munchnones, and sydnones. In general, analogous cycloadditions were also performed with acetylenic sulfones in solution phase for comparison. The cycloadditions typically afforded good to excellent yields of the desired products in both solution and solid phase, although the latter reactions sometimes required more vigorous conditions. Except in the case of benzyl azide and diazo compounds, where mixtures of regioisomers were obtained, the other 1,3-dipoles reacted with high regioselectivity and afforded essentially unique regioisomers. Cleavage of the products from the resin was smoothly effected by alkaline hydrolysis, while several attempts at reductive desulfonylation with sodium amalgam or samarium diiodide-HMPA resulted in N-O or C-O scission, in addition to cleavage from the polymer. The method provides access to a number of important classes of heterocycles, including variously substituted and functionalized triazoles, pyrazoles, 1,2-oxazoles, pyrroles, as well as their dihydro and bicyclic analogues. The success of the cycloadditions on polymer supports paves the way to future investigations of sequential transformations leading to libraries of useful heterocycles.

Solid-phase synthesis of β-keto sulfones

A novel method for the preparation of β-keto-sulfones through the use of organoselenium reagents in the solid phase by polystyrene-supported benzeneselenosulfonate or tolueneseleno-sulfonate with acetylenes has been developed. Georg Thieme Verlag Stuttgart.

Reactions of (E)-2-Iodo-1-tosyl-1-alkenes as Useful Synthetic Intermediates

(E)-2-Iodo-1-tosyl-1-alkenes readily available by iodosulfonization of 1-alkynes were found to be useful synthons for the regio- and/or stereoselective preparation of 1-tosyl-1-alkynes, 1-tosyl-2-alkynes, (Z)-vinyl and (Z)-allyl sulfones, β-tosyl enamines