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Relevant academic research and scientific papers

Copper-mediated sulfonylation of aryl iodides and bromides with arylsulfonyl hydrazides in PEG-400

Sulfonylation using stable and readily available arylsulfonyl hydrazides and aryl iodides or bromides mediated by cupric acetate has been achieved. Using polyethylene glycol (PEG-400) as an eco-friendly medium, the coupling reaction could afford a series of unsymmetrical diaryl sulfones in moderate to good yields without the presence of additional ligands and base.

Friedel - Crafts sulfonylation in 1-Butyl-3-methylimidazolium chloroaluminate ionic liquids

1-Butyl-3-methylimidazolium chloroaluminate ionic liquids have been employed as an unconventional reaction media and as Lewis acid catalyst for Friedel-Crafts sulfonylation reaction of benzene and substituted benzenes with 4-methyl benzenesulfonyl chloride. The substrates exhibited enhanced reactivity, furnishing almost quantitative yields of diaryl sulfones, under ambient conditions. Studies concerning the effect of Lewis acidity of the ionic liquid on the initial extent of conversion of this reaction has been carried out. 27Al NMR spectroscopy has been exploited as a tool to investigate the mechanistic details of the reaction. 27Al NMR spectral studies show the predominance of [Al2Cl7]- species in [bmim] Cl-AlCl3, N = 0.67, acidic ionic liquid in the presence of 4-methyl benzenesulfonyl chloride, and after the reaction with the aromatic hydrocarbon, [AlCl4]- species predominates. This change in speciation of aluminum can be attributed to the interaction of the Lewis acidic species [Al2Cl7]- of the ionic liquid with the formed HCl during the sulfonylation reaction, which is evidenced by the control experiment. Preliminary investigations on Friedel-Crafts acylation further substantiate the argument.

Sulfonylation of aromatic compounds with methyl p-toluenesulfonate as a sulfonylating precursor

We have developed Friedel-Crafts (FC) sulfonylation of aromatic compounds with methyl p-toluenesulfonate as a sulfonylating precursor. In this procedure, methyl p-toluenesulfonate was treated and activated with pyridine to produce N-methylpyridinium p-toluenesulfonate as a sulfonylation reagent. Reactivity of this salt for the sulfonylation of mesitylene was investigated in the presence of three different promoters, such as triflic anhydride, dimethylsulfide ditriflate, and triphenylphosphine ditriflate (TPPD). All of the promoters show chemoselectivity and among them, TPPD presents a chemoselectivity in FC sulfonylation. Iranian Chemical Society 2012.

Visible-light-driven electron donor-acceptor complex induced sulfonylation of diazonium salts with sulfinates

This work reports an efficient sulfonylation reaction enabled by a visible-light-induced radical coupling reaction between phenyl/heterocyclic diazonium salts and sulfinates. Mechanistic experiments disclosed the formation of a versatile electron donor-acceptor (EDA) complex. This transformation is characterized by an easy operational procedure under mild conditions which avoids transition metals, ligands, catalysts, and oxidants.

An efficient heterogeneous copper fluorapatite (CuFAP)-catalysed oxidative synthesis of diaryl sulfone under mild ligand- and base-free conditions

A simple, eco-friendly and efficient method for the synthesis of unsymmetrical diaryl sulfones using heterogeneous copper fluorapatite (CuFAP)-catalysed coupling of aryl sulfonic acid and phenyl boronic acid has been developed with good to excellent yields without use of any ligand, base or co-catalyst. Broad substrate scope and gram scale operations are the important features of this method.

Sulfonylation of aromatic compounds with sulfonic acids using silica gel-supported AlCl3 as a heterogeneous Lewis acid catalyst

Silica gel-supported aluminum chloride (SiO2-AlCl3) has been shown to be a mild, efficient, and chemoselective heterogeneous Lewis acid catalyst for direct conversion of arenes to sulfones using sulfonic acids as sulfonylating agents. The catalyst can be prepared easily with cheap starting materials and is stable (as a bench-top catalyst) and reusable.

Polystyrene supported Al(OTf)3: A stable, efficient, selective, and reusable catalyst for sulfonylation of arenes with sulfonic acids

Cross-linked polystyrene supported aluminium triflate (Ps-Al(OTf) 3) was found to be an efficient and chemoselective heterogeneous Lewis acid catalyst for the direct conversion of arenes to sulfones using sulfonic acids as sulfonylating agents. The solid acid catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency.

Highly selective catalytic Friedel-Crafts sulfonylation of aromatic compounds using a FeCl3-based ionic liquid

Friedel-Crafts sulfonylation of aromatic compounds was carried out using FeCl3-based ionic liquid. These liquids serve as efficient media as well as Lewis acid catalyst.