Cellulose Oxidation and the Use of Carboxyl Cellulose Metal Complexes in Heterogeneous Catalytic Systems to Promote Suzuki-Miyaura Coupling and C−O Bond Formation Reaction

Abstract

This work shows the modification of microcrystalline cellulose by the selective oxidation of primary hydroxyl groups to carboxylate groups by a 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO)-mediated system and its application as a heterogeneous ligand by ionic exchange with catalytic metals ions such as palladium, nickel and copper. Afterwards is described the application of the synthesized material as catalyst in coupling reactions such as Suzuki-Miyaura coupling and C−O bond formation reaction in different conditions, which are of great importance for the synthesis of drugs, natural products and new materials such as dendrimers, liquid crystals and polymers with magnetic and optical properties. The carboxyl cellulose matrix shows to have superior catalytic results as a ligand for all coupling reactions. Can be also highlighted the affinity of the carboxyl cellulose ligand in polar solvents such as water and alcohols and its application in mild conditions.

Wood-Sourced Polymers as Support for Catalysis by Group 10 Transition Metals

“…The selective oxidation of the primary hydroxyl groups of cellulose yields carboxyl cellulose (CC), which permits the direct coordination of metal ions [45]. CC has been used as a ligand to complex palladium or nickel ions.…”