Functionalized cellulose‐supported triphenylphosphine and its application in Suzuki cross‐coupling reactions

Abstract

A new heterogeneous cellulose tagged triphenylphosphine (Cell-OPPh 3 ) was synthesized and subsequently coordinated with Pd(OAc) 2 to form a cellulose-supported triphenylphosphine palladium complex (Cell-OPPh 3 -Pd). Cell-OPPh 3 and the corresponding palladium complex were fully characterized by TGA, SEM, TEM, and NMR analysis. Results of catalytic activity experiments indicate that the Cell-OPPh 3 -Pd complex can efficiently catalyze Suzuki-Miyaura cross-coupling reactions of aryl halides with arylboronic acids at mild reaction conditions. The coupling products can be obtained in good to excellent yields (up to 98%). The work-up procedure is simple and the catalyst could be easily recovered by filtration, and then reused in next run.

Nicotine functionalized‐silica palladium (II) complex: a highly efficient, environmentally benign and recyclable nanocatalyst for C‐C bond forming reactions under mild conditions

“…The product was isolated by column chromatography (n‐hexane / ethyl acetate, 5:1. The substituted biphenyls synthesized in this work are known compounds and were characterized by their IR, 1 H and 13 C NMR spectra, which have been reported previously in the literature …”

Recent Developments in the Immobilization of Palladium Complexes on Renewable Polysaccharides for Suzuki–Miyaura Cross-Coupling of Halobenzenes and Phenylboronic Acids

“…Wang et al [114] reported on the heterogenization of Pd(OAc) 2 on cellulose by immobilization of triphenylphosphine, which served as the ligand, to the polymer in three steps (Figure 17). conditions, K2CO3 was the best base and methanol the preferred solvent.…”

“…In each cycle, a slight loss of activity was observed from a 94% conversion rate obtained in the first run to 86% in the sixth run. Wang et al [114] reported on the heterogenization of Pd(OAc)2 on cellulose by immobilization of triphenylphosphine, which served as the ligand, to the polymer in three steps (Figure 17). FTIR spectra of the new catalyst indicated that a new C-O bond of Cell-OPPh3 was synthesized.…”

“…The success of grafting triphenylphosphine onto the cellulose backbone was also confirmed by CP/MAS 13 C-NMR and 31 P-NMR spectroscopy. Furthermore, thermogravimetric analysis evaluated the stability of the cellulose-supported catalyst in air and high temperature [114].…”

“…The yields of the catalyst products obtained in Suzuki cross-coupling, using different halobenzenes with phenylboronic acid derivatives in ethanol at 80 • C, ranged from 4% to 98% [114]. The reusability of the catalyst in the Suzuki-Miyaura coupling reaction of 4-bromoanisole with phenylboronic acid was also tested for four runs.…”