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

Indah Raya; Svetlana Danshina; Abduladheem Turki Jalil; Wanich Suksatan; Mustafa Z Mahmoud; Ali B Roomi; Yasser Fakri Mustafa; Milad Kazemnejadi

doi:10.1039/d2ra03440a

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

RSC Adv. 2022 Jul 12;12(31):20156-20173. doi: 10.1039/d2ra03440a. eCollection 2022 Jul 6.

Authors

Indah Raya¹, Svetlana Danshina², Abduladheem Turki Jalil³, Wanich Suksatan⁴, Mustafa Z Mahmoud^{5

6}, Ali B Roomi^{7

8}, Yasser Fakri Mustafa⁹, Milad Kazemnejadi¹⁰

Affiliations

¹ Department of Chemistry, Faculty of Mathematics and Natural Science, Hasanuddin University Makassar 90245 South Sulawesi Indonesia.
² Sechenov First Moscow State Medical University Moscow Russia.
³ Medical Laboratories Techniques Department, Al-Mustaqbal University College Babylon Hilla 51001 Iraq abedalazeem799@gmail.com.
⁴ Faculty of Nursing, HRH Princess Chulabhorn College of Medical Science, Chulabhorn Royal Academy Bangkok Thailand.
⁵ Department of Radiology and Medical Imaging, College of Applied Medical Sciences, Prince Sattam Bin Abdulaziz University Al-Kharj 11942 Saudi Arabia.
⁶ Faculty of Health, University of Canberra Canberra ACT Australia.
⁷ Ministry of Education, Directorate of Education Thi-Qar Thi-Qar Iraq.
⁸ Biochemistry and Biological Engineering Research Group, Scientific Research Center, Al-Ayen University Thi-Qar 64001 Iraq.
⁹ Department of Pharmaceutical Chemistry, College of Pharmacy, University of Mosul Mosul Iraq.
¹⁰ Department of Chemistry, Faculty of Science, Golestan University Gorgan Iran miladkazemnejad@yahoo.com.

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.