H₃PW₁₂O₄₀‐Catalysed Alkylation of Arenes and Diveratrylmethanes: Convenient Routes to Triarylmethanes and to Symmetrical and Unsymmetrical 9,10‐Diaryl‐2,3,6,7‐tetramethoxyanthracenes

Abstract

An efficient method for the synthesis of triarylmethanes and difurylarylmethanes through solventless reactions between aldehydes and arenes in the presence of H 3 PW 12 O 40 as a reusable catalyst under thermal and microwave irradiation conditions has been developed. H 3 PW 12 O 40 -catalysed onepot consecutive Friedel-Crafts reactions between veratrole and aldehydes were also applied as a convenient protocol for

Synthesis of new functionalized triarylmethanes via Suzuki cross-coupling and Heck-type vinylation reactions

“…The catalyst was separated by simple filtration, and the crude product was purified by recrystallization from EtOH. The products 10a [22,24,25], 10b [12], 10c [25], 10e [12], and 10h [21,26,27] have already been described and matched with bibliographic data. An oven-dried 25 mL two-neck flask equipped with a condenser and a magnetic stir bar was charged with Pd(PPh 3 ) 4 (5 mol%), TRAM 10 (1 mmol), and arylboronic acid 11 (1.2 mmol).…”

“…Additionally, stilbenoid units have been incorporated into a few tetraarylmethanes using Suzuki coupling reactions [20]. As part of an ongoing program on extending the synthetic applications of TRAMs [12,[21][22][23], we herein describe our efforts toward the functionalization of TRAMs via the Suzuki-Miyaura and Heck-type reactions of brominated TRAMs with arylboronic acids and olefins.…”

Practical Synthesis of Novel Symmetrical and UnsymmetricalTetrakis(aryl/heteroaryl) Adducts Containing Polyconjugated Linkages

“…In this regard, poly(4‐vinylpyridinium) hydrogen sulfate [P4‐VPH][HSO 4 ] has been used as a polymeric and reusable solid acid catalyst in several organic transformations [38] . In continuation of our ongoing program on developing N , N ‐bidentate TRAM‐based ligands for C−C coupling reactions, and synthesis of novel TRAMs, [35f–j,36a,b] we describe here the successful application of L5 as an air and moisture stable N ‐donor ligand in copper‐catalysed SMC reactions, and conversion of the derived products into TRAM‐based polyconjugated derivatives.…”

“…In recent years, a particular interest has been paid to the use of TRAMs as intermediate in organic synthesis [35a–l] or as ligand in catalysis reactions [35m,n] . Although, a number of protocols are available for the syntheses of tetrakis (aryl/heteroaryl) adducts, [35f–l,36] to the best of our knowledge, no report to date addresses the synthesis of their respective analogues containing polyconjugated linkages.…”

“…The F−C alkylation of o ‐hydroxy bisbenzylic alcohols with aromatic or heteroaromatic arenes under solvent free conditions and indium(III) triflate catalysis has been developed by Mondal et al to achieve the corresponding unsymmetrical TRAMs [34g] . In recent years, a particular interest has been paid to the use of TRAMs as intermediate in organic synthesis [35a–l] or as ligand in catalysis reactions [35m,n] . Although, a number of protocols are available for the syntheses of tetrakis (aryl/heteroaryl) adducts, [35f–l,36] to the best of our knowledge, no report to date addresses the synthesis of their respective analogues containing polyconjugated linkages.…”