Iminophosphine palladium catalysts for Suzuki carbonylative coupling reaction

• Published in: Applied organometallic chemistry Vol. 32; no. 2
• Main Authors: Yılmaz, Mustafa Kemal, Keleş, Hülya, İnce, Simay, Keleş, Mustafa
• Format: Journal Article
• Language: English
• Published: Chichester Wiley Subscription Services, Inc 01.02.2018
• Subjects: Acetonitrile; Aromatic compounds; Carbon monoxide; Carbonyls; Catalysis; Catalysts; Chemical reactions; Chemistry; Cross coupling; Electrochemical analysis; electrochemistry; Fourier transforms; iminophosphines; Iodides; Nitrogen atoms; NMR; Nuclear magnetic resonance; Palladium; Suzuki carbonylation
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.4002

Three iminophosphine ligands having soft phosphorus and hard nitrogen atoms and their Pd(II) complexes were synthesized and characterized using 1H NMR, 13C NMR, 31P NMR and Fourier transform infrared spectroscopic techniques. Also, electrochemical properties of the iminophosphines and their Pd(II) complexes were investigated in acetonitrile–tetrabutylammonium perchlorate solution with cyclic and square wave voltammetry techniques. All Pd(II) complexes were evaluated as catalysts for carbonylative cross‐coupling reactions of aryl iodides with phenylboronic acid. The Suzuki carbonylation of aryl iodides at 80 °C under balloon pressure of carbon monoxide in the presence of K2CO3 as a base was examined, and good to high conversions and excellent selectivities were obtained. Three iminophosphine ligands and their Pd(II) complexes were synthesized and characterized. Electrochemical properties of the iminophosphines and their Pd(II) complexes were investigated in acetonitrile–tetrabutylammonium perchlorate solution with cyclic and square wave voltammetry techniques. All Pd(II) complexes were evaluated as catalysts for carbonylative coupling reactions of aryl iodides with phenylboronic acid at 80 °C under balloon pressure of carbon monoxide in the presence of K2CO3 as a base and good to high conversions and excellent selectivities were obtained.