Imidazolium ionic liquid-tagged palladium complex: an efficient catalyst for the Heck and Suzuki reactions in aqueous media

Abstract

An air stable, water soluble, and efficient ionic liquid-tagged Schiff base palladium complex was prepared.The synthesized complex was well characterized by NMR, mass spectrometry, FT-IR, UV-visible spectroscopy and powder X-ray diffraction. The complex was used as a catalyst for the Suzuki and Heck crosscoupling reactions in water. Good to excellent yields were achieved using a modest amount of the catalyst. In addition, the catalyst can be easily reused and recycled for six steps without much loss in activity, exhibiting an example of sustainable and green methodology.H and 13 C NMR, and mass spectrometry data for the ionic liquid-supported Schiff base (4) and its Pd complex (5), and 1 H and 13 C NMR data for 8 & 10. See

An Ionic Liquid Immobilized Palladium Complex for an Effective Heck and Suzuki Coupling Reactions

“…For example, 4-nitro, 4-methyl, 4-methoxy and 2-aminoiodobenzenes were converted easily to the corresponding coupled products. The above findings were comparable to the previously reported results of widely used procedures [45][46][47][48][49][50][51]. The advantage for the present work lies in the less reaction time compared to previously reported results and also gave a high yield for over a range of products.…”

Physico-chemical characterization and biological studies of newly synthesized metal complexes of an Ionic liquid-supported Schiff base: 1-{2-[(2-hydroxy-5-bromobenzylidene)amino]ethyl}-3-ethylimidazolium tetrafluoroborate

“…In the ESI-MS spectrum, the Cu(II) complex (5) exhibited a peak (m/z) at 705.74 which is assigned to the [M-BF 4 ] + ion. 43 (The ESI-MS spectra of the complexes and ligand are given in Figures S1 and S2 in Supplementary Information). The mass spectra of the ligand and complexes were in good agreement with the respective structures as revealed by the elemental and other spectral analyses.…”

Application of Curcumin as Ligand in [Pd(Curc‐H)2] Catalyst for Carbon‐Carbon Bond Formation in Heck and Suzuki Coupling Reactions

“…Various methods are present for Heck reaction with several metal‐metal complexes and ligands like palladium complex of PdCl 2 (bipy), palladium N‐heterocyclic bis‐carbene (Pd‐NHDC) moiety containing a UiO‐67 type MOF (UiO‐67‐Pd‐NHDC) catalyst, cellulose supported poly(hydroxamic acid) Pd(II) complex, complex of PdCl 2 with a multidentate cryptand ligand (Kryptofix 5), triphenylphosphine and tris(2‐furyl)phosphine with fluorinated palladium sources, tridentate SCS palladium(II) complexes, palladacycles, oximecarbapalladacycle, Pd/C in ionic liquid, N,N‐dimethyl‐ β ‐alanine with Pd(OAc) 2 , N‐phenylurea with Pd(OAc) 2 , silica‐supported palladium catalyst, Pd(quinoline‐8‐carboxylate) 2 , pyrazolyl‐functionalized carbene palladium complexes, Pd anchored on L‐proline‐functionalized silica gel as catalyst, 2‐aminophenyl diphenylphosphinite with Pd(OAc) 2 , trans ‐[PdCl 2 (DEA) 2 ], thiadiazolidine1‐oxide with Pd 2 (dba) 3 , 2,2‐diamino‐6,6‐dimethylbiphenyl with Pd(OAc) 2 , cationic 2,2’‐bipyridyl ligand, amino oxazoline ligands with Pd(OAc) 2 , Pd(L‐Proline) 2 , complexes of Pd and Cu with 2‐(2’‐hydroxyphenyl)‐5,6‐dihydro‐1,3‐oxazine, Pd 2 (dba) 3 with methyl 4,6‐ O ‐benzylidene‐3‐deoxy‐3‐(diphenylphosphino)‐α‐D‐altropyranoside, InCl 3 , tridentate Schiff base palladium(II) complex, imidazolium ionic liquid‐tagged Schiff base palladium complex, Pd(OAc) 2 with N ‐(1‐methylpyridin‐4(1 H )‐ylidene)amine ligands, and several catalysts systems without ligand…”