Organosulphur and related ligands in Suzuki–Miyaura C–C coupling

Abstract

Suzuki-Miyaura C-C cross coupling (SMC), an important synthetic strategy for many organic molecules, has several advantages such as mild reaction conditions, high tolerance toward various functional groups and ease in isolation of the product. Palladium(II) ligated with phosphines (particularly bulky and electron-rich) and N-heterocyclic carbenes (NHCs) has been found to be efficient in the catalysis of SMC. The drawback with many of these catalysts is their air/moisture sensitivity. Since 2000, palladium(II) complexes of organosulphur and related ligands have emerged as viable alternatives to palladium-phosphine/carbene complexes as they have sufficient thermal stability, air and moisture insensitivity. Moreover synthesis of complexes of such ligands is easy. In this perspective Suzuki-Miyaura C-C coupling reactions catalyzed with palladium(II)-complexes of organosulphur ligands have been reviewed. Catalysis of SMC with palladium(II) complexes of organoselenium and tellurium ligands, studied much less in comparison to those of organosulphur ligands, is also included.

Suzuki Coupling Reactions Catalyzed with Palladacycles and Palladium(II) Complexes of 2‐Thiophenemethylamine‐Based Schiff Bases: Examples of Divergent Pathways for the Same Ligand

“…Palladacycles and Pd II complexes ( 1–5 ) of these ligands have been prepared and explored for Suzuki–Miyaura coupling reactions. The in situ formation of Pd‐containing NPs has been reported in Suzuki–Miyaura coupling reactions catalyzed with palladacycles9b of the organosulfur ligand as well as Pd complexes of sulfated Schiff bases 12c …”

Computational investigations of click-derived 1,2,3-triazoles as keystone ligands for complexation with transition metals: a review

“…The calculated geometrical data clearly indicated that the change in the squareplanar core was not considerable when going from the anti (27) to the syn (29) conformer; except the Pd-N2 bond, which was slightly elongated to 0.014Å.…”

“…Recently, the promise of metal complexes of organo 1,2,3-triazole-based ligands has been demonstrated in the catalysis of some chemical transformations, 27,28 such as hydroformylation and intramolecular hydroamination.…”

Efficient Suzuki–Miyaura C-C Cross-Couplings Induced by Novel Heterodinuclear Pd-bpydc-Ln Scaffolds

“…The reaction has long been the subject of vast research in transition-metal catalysis. Various transition metal complexes [71,72,73,74,75,76,77,78,79] (e.g., Ni, Au, Co, Cu, etc., as such or combined in pairs as heterobimetallic catalysts), or nonconventional Pd(II)-complexes with intricate organic ligands containing S or Se have been intensively explored [80,81]. Efficient transition metal-free catalysts have also been reported for Suzuki–Miyaura cross-coupling reactions [82].…”