Synthesis of functionalized triarylmethanes based on a ‘FeCl3-catalyzed benzylation/[3+3] cyclocondensation’ strategy

Direct Nucleophilic SN1‐Type Reactions of Alcohols

“…[71] The compounds are useful starting materials for the synthesis of functionalized triarylmethane. [72] The reaction of propargylic alcohols with a series of nucleophiles was reported by Jana. The use of FeCl 3 (5 mol-%) in CH 3 CN allowed the direct substitution of propargylic alcohols with C, O, N, and S nucleophiles.…”

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

“…159 14.7 3 + 3 Cyclocondensation for the preparation of triarylmethanes P. Langer et al in 2009 reported ferric chloride catalyzed benzylations with diarylmethanols to prepare 3-(diaryl methyl) pentane 2,4-diones followed by formal [3 + 3] cyclizations with 1,3-bis(1,3-trimethylsilyloxy)-1,3-dienes to prepare highly functionalized triarylmethanes that are inaccessible by conventional synthetic approaches (Scheme 117a). 160,161 In order to explain the reaction pathway, the author proposed the following mechanism (Scheme 117b). At rst the pentane diones react with diarylmethanols in presence of ferric chloride to form the 3-(diaryl methyl) pentane-2,4-diones (55A).…”

Copper‐Catalyzed Arylation of Olefins Using a Novel N,N‐Bidentate TRAM‐Based Ligand: Application in Synthesis of Functionalized Triarylmethanes[]**

“…[44][45][46][47][48][49] They are traditionally synthesized via the Friedel-Crafts alkylation of arenes with aldehydes or diarylmethanoles assisted by Lewis acids, [50] Brönsted acids, [51] or other species. [52] TRAMs, on the other hand, have been prepared employing several alternative methods including benzylation/[3 + 3] cyclocondensation reaction catalyzed by FeCl 3 , [53] Baeyer condensation of aldehydes and N,N-dimethylaniline catalyzed by an amide-based ionic liquid, [54] or in the presence of atomized sodium in THF, [55] Vicarious nucleophilic substitution of hydrogen, [56] reaction of chlorohydrocarbon with different nucleophiles promoted by fluorinated alcohol, [57] and transition metal-catalyzed cross-coupling reactions. [58] FeCl 3 -catalyzed dual CÀ C bond cleavage reaction of diarylmethane derivatives involving two efficient carbon-based leaving groups has been reported by Paul et al for the synthesis of symmetrical and unsymmetrical TRAMs.…”