Cobalt pincer complex catalyzed Suzuki-Miyaura cross coupling – A green approach

Abstract

A series of cobalt complexes with tridentate pincer ligands were synthesized to study their catalytic activity in Suzuki-Miyaura coupling reactions. Cobalt complexes, C-1, C-2, C-3 bearing asymmetrical PNCOP pincer ligand [C<inf>6</inf>H<inf>4</inf>-1-(NHPPh<inf>2</inf>)-3-(OPPh<inf>2</inf>)] (L-1) and symmetrical PNCNP, PNNNP pincer ligands [C<inf>6</inf>H<inf>4</inf>-2,6-(NHPPh<inf>2</inf>)<inf>2</inf>] (L-2) and [C<inf>5</inf>H<inf>3</inf>N-2,6-(NHPPh<inf>2</inf>)<inf>2</inf>] (L-3) were synthesized by the reaction of diphenylchlorophosphine with m-aminophenol, m-phenylenediamine and 2,6-diaminopyridine respectively in a 1:2 ratio in the presence of triethylamine as a base and tetrahydrofuran as solvent media. The synthesized complexes were examined for their C-C coupling efficiency in cross-coupling between phenyl boronic acid and para substituted bromobenzenes. Effect of variation of the ligand on the catalytic activity of cobalt pincer complex was explored based on the coupling yields. It is observed that as the number of ‘N’ atoms increases in the side arm of the ligand, the donating ability of the ligand increases which leads to the increased catalytic activity of the complex. The symmetrical PNNNP pincer complex (C-3) was found to be more effective as a catalyst among the complexes synthesized and reported in the present study. © 2016 Elsevier B.V.