Introduction of a Recyclable Basic Ionic Solvent with Bis-(NHC) Ligand Property and The Possibility of Immobilization on Magnetite for Ligand- and Base-Free Pd-Catalyzed Heck, Suzuki and Sonogashira Cross-Coupling Reactions in Water

• Published in: Catalysis letters 2021-10, Vol.151 (10), p.3030-3047
• Main Authors: Min, Qingwang, Miao, Penghua, Chu, Deyu, Liu, Jinghan, Qi, Meijuan, Kazemnejadi, Milad
• Format: Article
• Language: English
• Subjects: Axitinib; Catalysis; Catalysts; Catalytic activity; Chemical reactions; Chemistry; Chemistry and Materials Science; Cross coupling; Hydroxides; Industrial Chemistry/Chemical Engineering; Ion exchange; Ligands; Magnetic properties; Magnetite; Olopatadine hydrochloride; Organometallic Chemistry; Palladium; Phenolphthalein; Physical Chemistry; Precursors; Solvents
• ISSN: 1011-372X; 1572-879X
• DOI: 10.1007/s10562-021-03552-5

A new versatile and recyclable NHC ligand precursor has been developed with ligand, base, and solvent functionalities for the efficient Pd-catalyzed Heck, Suzuki and Sonogashira cross-coupling reactions under mild conditions. Furthermore, NHC ligand precursor was immobilized on magnetite and its catalytic activity was also evaluated towards the coupling reactions as a heterogeneous catalyst. The NHC ligand precursor was prepared with imidazolium functionalization of TCT followed by a simple ion exchange by hydroxide ions. However, the results revealed an excellent catalytic activity for the both homogeneous and heterogeneous catalytic systems. 1.52 g.cm −3 and 1194 cP was obtained for the density and viscosity of the NHC ligand precursor respectively. On the other hand, the heterogeneous type could be readily recovered from the reaction mixture and reused for several times while preserving its properties. Heterogeneous nature of the magnetic catalyst was studied by hot filtration, mercury poisoning, and three-phase tests. High to excellent yields were obtained for all entries for the both homogeneous and heterogeneous catalysts, which reflects the high consistency of the catalyst. Graphic Abstract