Brönsted acid-catalyzed synthesis of diarylmethanes under non-genotoxic conditions

Synthetic methodologies of achiral diarylmethanols, diaryl and triarylmethanes (TRAMs) and medicinal properties of diaryl and triarylmethanes-an overview

“…Ghosez et al in 2011 reported Brønsted acid catalyzed arylation of benzyl acetates and anisyl acetates with arenes for the preparation of diarylmethanes (Scheme 29). 45 Triuoromethane sulfonic acid and triimide respectively were used as the Bronsted acid catalyst. Except for the triimide, the reactions were carried out without the use of solvent.…”

Triflimide (HNTf2) in Organic Synthesis

“…In a related reaction, Ghosez and co-workers described a benzylation of electron-rich arenes employing benzylic acetates as the carbocation precursor (Scheme ). This reaction provided a rapid and efficient approach to synthesize diarylmethanes, an important family of compounds often with useful biological activity …”

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

“…Subsequently we examined various aromatic substrates with benzyl acetate as electrophile under solvent-free conditions and with solvent using SSA or [Msim]AlCl 4 as catalyst (Table 3). In certain instances, reaction occurred 7 However, with our protocol, 3-benzyl indole was obtained in good yield using [Msim]AlCl 4 or SSA as catalyst (Table 3, entry 6). Generally, our protocol is more efficient than previous methods; 16 with substrates possessing additional electron-donating groups, the yield increased and reaction time decreased (Table 3, entries 1 and 2) and, with phenol as substrate, the p-benzylphenol was produced rather than the o-benzylphenol.…”

“…[1][2][3] Catalytic systems used for the benzylation of aromatic compounds include HfO 2 -HfCl 4 , 3 aliquat 336, 4 phosphomolybdic acid supported silica gel, 5 TMSOTf, 6 organozinc and organoboron derivatives, HCl, H 2 SO 4 , MeSO 3 H, HOTf and HNTf 2 . 7 However, some of these procedures suffer from various drawbacks, such as complex workup and purification, production of significant amounts of waste materials, use of strongly acidic conditions, and occurrence of side reactions with poor yields. In recent years, silica sulfuric acid (SSA), as one of the more important solid acid catalysts, [8][9][10][11][12] and 3-methyl-1sulfonic acid imidazolium tetrachloroaluminate ([Msim]AlCl 4 ), as a new sulfonic acid functionalized imidazolium salts (SAFIS) with interesting applications, have been reported (Figure 1).…”