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

Abstract

3,3'-((phenylmethylene)bis(4-methoxy-3,1-phenylene)) dipyridine L was used as a novel N,N-bidentate triarylmethanebased ligand in Mizoroki-Heck reactions. This air and moisture stable ligand was identified as a useful alternative to the commonly used phosphine ligands. The in-situ generated complex of L with Cu(OAc) 2 showed excellent activity in cross coupling of aldehydes with olefins and a selected library of formylated olefins was prepared in high yields. The Friedel-Crafts alkylation of arenes with the derived olefins catalyzed by Fe(OTs) 3 was also employed for the preparation of functionalized triarylmethanes. This alternative method offers several important advantages including mild reaction conditions, short reaction times, high yields, simple work-up procedure, and broad substrate scope.

Practical Synthesis of Novel Symmetrical and UnsymmetricalTetrakis(aryl/heteroaryl) Adducts 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.…”