Abstract
Chloroaluminate ionic liquid bound on magnetic nanoparticles (Fe3O4@O2Si[PrMIM]Cl·AlCl3) was prepared and used as a heterogenous Lewis acidic catalyst for the Friedel–Crafts sulfonylation of aromatic compounds with sulfonyl chlorides or p-toluenesulfonic anhydride. The catalyst’s stability, efficiency, easy recovery, and high recyclability without considerable loss of catalytic capability after four recycles were evidence of its advantages. Furthermore, the stoichiometry, wide substrate scope, short reaction time, high yield of sulfones, and solvent-free reaction condition also made this procedure practical, ecofriendly, and economical.
Highlights
Widespread synthetic routes of sulfones via the oxidation of the corresponding sulfides or sulfoxides [12–14], the sulfonylation of chloropyridine derivatives by sulfinate salts [15], the arylation of sulfinate salts by diaryliodonium salts [16], the formation of a C–S bond via the reaction of various silyl triflate and arenesulfinate salts [17], the addition to alkynes by sulfinate salts [18], the oxidative cyclization of phenyl propiolates with sulfinic acids initiated by visible light [19], the decarboxylative C–S cross-coupling of cinnamic acid with benzenesulfinate salts promoted by iodine [20], and the Friedel–Crafts sulfonylation have been developed
Among numerous approaches to sulfone preparations, aryl sulfones have been synthesized, preferably via the Friedel–Crafts sulfonylation reactions between activated arenes and sulfonylating reagents in the presence of catalysts; e.g., Lewis acidic salts [21–26], Zn [27], In/dioxane [28], MoO2 Cl2 [29], metal triflate [30,31], Fe(OH)3 [32], nafion-H [33], Fe(III)-exchanged montmorillonite [34], Ps-AlCl3 and SiO2 -AlCl3 [35,36], Lewis acidic salt-based ionic liquids [37,38], and P2 O5 supported on Al2 O3 [39] or SiO2 [40]
At the beginning of this work, based on the the disadvantages disadvantages of cling of the chloroaluminate ionic liquid used for the Friedel–Crafts sulfonylation between cling of the chloroaluminate ionic liquid used for Friedel–Crafts sulfonylation between cling of the chloroaluminate ionic liquid used for the Friedel–Crafts sulfonylation between toluene toluene and and benzenesulfonyl benzenesulfonyl chloride chloride [59]
Summary
One of the most common organosulfur compounds, have tremendous applications in chemical processes [1,2], medicinal chemistry, and drug syntheses owing to their various biological activities; for instance, anti-inflammatory [3,4], anti-HIV [5], antimalarial [6,7], anticancer [8], and antimicrobial [9,10], and as a cysteine protease inhibitor [11]. Contrarily, heterogeneous heterogeneous catalysts catalysts fore could be recovered and recycled conveniently and efficiently, their dispersion could be recovered andconveniently recycled conveniently and efficiently, their in dispersion recovered and recycled and efficiently, their dispersion reaction in reaction reaction media media have have not not been been carried carried out out well. To overcome overcome these these problems problems in in the the disdisin media have not been carried out well.
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