Benzylation of Aromatic Compounds Catalyzed by 3-Methyl-1-sulfonic Acid Imidazolium Tetrachloroaluminate and Silica Sulfuric Acid under Mild Conditions

Abstract

In this work, efficient procedures for benzylation of a range of aromatic compounds by benzyl acetate in the presence of catalytic amounts of 3-methyl-1-sulfonic acid imidazolium tetrachloroaluminate ([Msim]AlCl 4 ) or silica sulfuric acid (SSA) under mild conditions are described. Simple methodology, easy workup procedure, clean reaction and reusability of the catalyst are some advantages of this work.

Design, synthesis, and application of 1H-imidazol-3-ium trinitromethanide {[HIMI]C(NO2)3} as a recyclable nanostructured ionic liquid (NIL) catalyst for the synthesis of imidazo[1,2-a]pyrimidine-3-carbonitriles

“…We have previously investigated on the design, synthesis, applications, and development of green nanostructured, ionic liquids, molten salts, and organocatalysts for organic functional group transformations as well as for eco-friendly multicomponent synthesis of biologically important heterocyclic compounds. [37][38][39][40][41][42][43][44][45][46][47] Due to the above mentioned advantages of multicomponent reactions and ionic liquids, an eco-compatible imidazo[1,2-a]pyrimidine derivatives synthesis involving both methodologies would be highly desirable. [48] Herein, we report the synthesis of a green, mild, efficient, and reusable nanostructured ionic liquid catalyst, namely 1H-imidazol-3-ium trinitromethanide {[HIMI]C(NO 2 ) 3 } (1) (scheme 1) [49] and its application to the one-pot three component synthesis of 4-amino-1,2-6 dihydrobenzo [4,5]imidazo [1,2-a] To a round-bottomed flask (50 mL) containing imidazole (5.0 mmol, 340 mg) and CHR 3 RCN (5 mL, 1R M R), trinitromethane (5.0 mmol, 755 mg) was added drop wise.…”

Reductant‐Free Cross‐Electrophile Synthesis of Di(hetero)arylmethanes by Palladium‐Catalyzed Desulfinative C−C Coupling

“…[7] Due to use of organometallic species, these routes are often not amenable to complex functionality. Alternative methods, which often display low selectivity, include acid [8] or base-promoted benzylation, [9] radical-radical cross-coupling reactions, [10] and CÀ H activation approaches. [11] Suzuki-Miyaura type cross-couplings [12] suffer from the use of unstable benzylic boronate reagents and narrow scopes.…”

Regioselective Sulfonation of Aromatic Compounds over 1,3-Disulfonic Acid Imidazolium Chloride under Aqueous Media

“…Recently, sulfonic acid functionalized imidazolium salts (SAFIS) have been prepared and characterized as a new group of acidic ionic liquids and applied as solvents, cata-lysts, and reagents in organic transformations for the preparation of bis(indolyl)methanes, 14 N-sulfonyl imines, 15 1-amidoalkyl-2-naphthols, 16 xanthene derivatives, 17 1-carbamatoalkyl-2-naphthols, 18 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s, 19 N-Boc-protected amines, 20 hexahydroquinolines, 21 nitroaromatic compounds, 22,23 1,2,4,5-tetrasubstituted imidazoles, 24 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles, 25 benzylated aromatic compounds, 26 β-acetamido ketones, 27 benzimidazoles, 28 and amido-alkyl phenols. 29 Herein, we introduce 1,3-disulfonic acid imidazolium chloride ([Dsim]Cl), by simple reaction of imidazole (1 equiv) with chlorosulfonic acid (2 equiv) at room temperature (Scheme 1) as a sulfonic acid functionalized imidazolium salt (SAFIS) [14][15][16] and a highly efficient reagent for the sulfonation of aromatic compounds at 50 °C in aqueous medium.…”