Cu(OAc)2-porphyrins as an efficient catalytic system for base-free, nature mimicking Chan-Lam coupling in water

The use of porphyrins as ligands in organic synthesis reveals the natural process, because these are the constituent motifs of catalysts in many bio-organic reactions. This article presents the synthesis of two N-pincer tetradentate porphyrins; tetrasodium meso-tetra(p-sulfonatophenyl)phorphyrin (H(2)TSTpSPP) and meso-tetra(m-carboxyphenyl)porphyrin (H2TmCPP), and study on their aptness for Cu-catalyzed C-N coupling reactions of arylboronic acids and amines (Chan-Lam coupling reaction) in water under external base free conditions. The porphyrins and Chan-Lam coupling products were well characterized by their spectral analysis. The high product yields, application of nature-inspired conditions, large extent of substrates, ease of making and handling the ligands, avoidance of base, and use of water as reaction media are the attractive attributes of this finding.

Automated summary

The article introduces the synthesis of two new porphyrin ligands and their application in Chan-Lam coupling reactions in water. The method shows high product yields, ease of preparation and handling, avoidance of base, among other advantages.