Catalytic filtration: efficient C-C cross-coupling using Pd(II)-salen complex-embedded cellulose filter paper as a portable catalyst

Abstract

A new approach has been developed for environmentally friendly C-C cross-coupling reactions using bi-functional Pd(II)-salen complex-embedded cellulose filter paper (FP@Si-Pd^II-Salen-[IM]OH). A Pd(II)-salen complex bearing imidazolium [OH]⁻moieties was covalently embedded into a plain filter paper, then used as an efficient portable catalyst for the Heck, Suzuki, and Sonogashira cross-coupling reactions under environmentally friendly conditions via the filtration method. The catalytic filter paper properties were studied by EDX, XPS, TGA, ATR, XRD, and FESEM analyses. The reactions were catalyzed during reactants' filtration over the catalytic filter paper. The modified filter paper was set up over a funnel and the reactants were passed through the catalytic filter paper several times. The effect of reaction parameters including loading of Pd(II)-salen complex, temperature, solvent, and contact time were carefully studied and also the optimal model of conditions was presented by the design expert software. High to excellent yields were obtained for all C–C coupling types with 5 to 8 filtration times. Under optimal conditions, all coupling reactions showed high selectivity and efficiency. Another advantage of the modified filter paper was its stability and reusability for several times with preservation of catalytic activity and swellability.