78904-63-9

Upstream product

• 873-55-2 sodium benzenesulfonate 
• 86031-21-2 phenyl α-chlorododecylsylfone 
• 143-15-7 1-dodecylbromide 
• 124-22-1 n-Dodecylamine 
• 56056-49-6 (n-dodecylthio)benzene 
• 112-41-4 1-dodecene 
• 5535-48-8 PVS 
• 102710-12-3 1-dodecylsulfanylmethylbenzene 
• 112-53-8 1-dodecyl alcohol 

Downstream Products

• 112-41-4 1-dodecene 
• 112-54-9 Dodecanal 
• 87837-51-2 1-benzenesulfonyl 1-dodecene E 
• 2437-56-1 1-tridecene 
• 667870-38-4 ((1R,2S)-6-Benzenesulfonyl-1-benzyloxymethyl-2-hydroxy-5-oxo-heptadecyl)-carbamic acid benzyl ester 
• 853569-40-1 3-benzenesulfonyl-1,1,1-trifluoro-tetradecan-2-one 
• 914090-62-3 (2-hydroxy-1-methyl-5-oxo-heptadecyl)-carbamic acid benzyl ester 
• 26944-42-3 1,1,1,-trifluorotetradecan-2-one 
• 14058-54-9 (-)-deoxoprosophylline 
• 667870-39-5 ((1R,2S)-1-Benzyloxymethyl-2-hydroxy-5-oxo-heptadecyl)-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Cyanide-Mediated Synthesis of Sulfones and Sulfonamides from Vinyl Sulfones

We report a facile synthesis of sulfones, β-keto sulfones, and sulfonamides from vinyl sulfones via an addition-elimination sequence where in situ generation of nucleophilic sulfinate ion is mediated by cyanide. The use vinyl sulfones renders high selectivity for S -alkylation to produce sulfones in high yields. In the presence of N -bromosuccinimide, primary and secondary amines underwent sulfonamide formation. A preliminary mechanistic study showed the formation of acrylonitrile as an innocent byproduct, without interfering with the desired reaction pathway while generating a sulfinate nucleophile.

Hydrosulfonylation of Unactivated Alkenes by Visible Light Photoredox Catalysis

The anti-Markovnikov hydrosulfonylation of unactivated alkenes with sodium sulfinates was realized via [Ir(dF(CF3)ppy)2(dtbbpy)]PF6-mediated visible light photoredox catalysis. The presence of an acid such as acetic acid is essential for the reaction to take place. A variety of unactivated alkenes can be transformed into sulfones with good yield and high regioselectivity using this reaction, which is proposed to proceed by a radical mechanism.

The highly selective metal-free oxidation of sulfides, tellurides and phosphines using sodium bromate in the presence of recyclable ionic liquid [bmim]HSO4, at 80°C

The metal-free oxidation of sulfides to sulfones using sodium bromate (NaBrO3) in [bmim]HSO4:H2O (3:1, v/v) at 80°C is reported. Phenylalkyl, phenylbenzyl, diaryl and heteroaryl sulfides were transformed to the corresponding sulfones. Aryl tellurides and phosphines were oxidised to the corresponding telluroxides and phosphine oxides. All the reactions proceeded smoothly and gave high yields in 20-55 min. The ionic liquid [bmim]HSO4 was easily recovered and recycled.

Investigation of steric and electronic effects in the copper-catalysed asymmetric oxidation of sulfides

Steric and electronic effects in the copper-catalysed asymmetric oxidation of aryl benzyl, aryl alkyl and alkyl benzyl sulfides have been investigated. The presence of an aryl group directly attached to the sulfur is essential to afford sulfoxides with high enantioselectivities, with up to 97% ee for 2-naphthyl benzyl sulfoxide, the highest enantioselectivity achieved to date for copper-catalysed asymmetric sulfoxidation. In contrast, the benzyl substituent can be replaced by sterically comparable groups with no effect on enantioselectivity. Copper-mediated oxidation of substituted aryl benzyl sulfides display modest steric and electronic effects resulting in comparable or lower enantioselectivities to those obtained with the unsubstituted benzyl phenyl sulfide.

Highly atom-economic, catalyst- and solvent-free oxidation of sulfides into sulfones using 30% aqueous H2O2

Highly atom-efficient oxidation of sulfides into sulfones under solvent- and catalyst-free reaction conditions using a 30% aqueous solution of H 2O2 at 75 °C is reported. A structurally diverse set of phenyl alkyl-, phenyl benzyl-, benzyl alkyl-, dialkyl-, heteroaryl alkyl- and cyclic sulfides were transformed into sulfones regardless of the aggregate state and electronic nature of the substituents. In spite of the heterogeneous reaction mixtures throughout the work, no difficulties with stirring and reaction progress were noted. In numerous cases, only 10 mol% excess of H 2O2 was used, thus contributing considerably to the high atom economy of the process. Some solid substrates required a variable excess of hydrogen peroxide; however, the reactions were performed strictly without organic solvents. The transformation was demonstrated to be amenable for scale-up with both liquid and solid sulfides. In addition, isolation and purification of the crude products can be simply done with only filtration and crystallization.

Aqueous sodium hypochlorite mediated chemoselective oxidation of chalcogenides to monoxides and dioxides by microwave exposure

A solvent-free, rapid, and highly selective oxidation of sulfides, selenides, and tellurides (chalcogenides) to the corresponding monoxides (sulfoxides, selenoxides, and telluroxides) or the corresponding dioxides (sulfones, selenones, and tellurones) has been developed using aqueous sodium hypochlorite on solid supports by exposure to microwave. Chemoselectivity and quantitative yields have been attained in most cases.

An asymmetric aminohydroxylation route to cis-2,6-disubstituted piperidine-3-ol: application to the synthesis of (-)-deoxocassine

A highly efficient, flexible, and convergent route to cis-2,3,6-trisubstituted piperidines has been developed employing the Sharpless asymmetric aminohydroxylation and stereoselective reductive amination by catalytic hydrogenation as the key steps. Its usage is illustrated by the short synthesis of the piperidine-3-ol alkaloid, (-)-deoxocassine.

A new, practical and efficient sulfone-mediated synthesis of trifluoromethyl ketones from alkyl and alkenyl bromides

We report herein a new and efficient method to prepare trifluoromethyl ketones from the corresponding bromides through sulfones in good yields.

One-pot synthesis of aryl sulfones from alcohols

A one-pot synthesis of aryl sulfones from primary alcohols is described. Alcohols were treated with N-bromosuccinimide and triphenylphosphine, followed by addition of sodium arenesulfinate with a catalytic amount of tetrabutylammonium iodide to afford the aryl sulfones in good to high yields.

α-bENZENESULFONYL FREE RADICALS

Allylic α-halosulfones give, on reduction with tri n-butyl tin hydride, sizeable amounts of dimers.It so appears that free radicals can indeed be formed α to an arenesulfonyl group and coupling can occur during tin hydride reduction of halides