Palladium Nanoparticle‐Immobilized Porous Polyurethane Material for Quick and Efficient Heterogeneous Catalysis of Suzuki‐Miyaura Cross‐Coupling Reaction at Room Temperature

Abstract

Here we report, room temperature heterogeneous catalysis of the Suzuki‐Miyaura cross‐coupling reaction by a Pd0 nanoparticle‐immobilized porous organic polymer (TPU‐Pd), providing excellent yields (up to 99%) using low catalyst loading. High nitrogen‐ and oxygen‐donor content of triazine‐based porous polyurethane (TPU) makes it an efficient porous polymer for Pd‐immobilization and subsequent heterogeneous catalysis of C–C cross‐coupling reactions. X‐ray photoelectron spectroscopy of TPU‐Pd showed characteristic binding energy peaks of Pd0. Atomic absorption spectroscopy revealed 10.4 wt% of Pd0 in TPU‐Pd, and transmission electron microscopy images showed well‐dispersed and facetted Pd0 nanoparticles of size 5–20 nm. Catalysis of Suzuki‐Miyaura reaction was observed to be completed in 3 h at 25 °C for a wide range of aryl halide substrates with phenylboronic acid, whereas increasing the reaction temperature to 80 °C largely allows decreasing the reaction time to 0.5‐1 h. The porosity and surface area of the catalyst was not affected after catalysis, and the catalyst has been reused for five consecutive runs.

Role of Polymer Structures in Catalysis by Transition Metal and Metal Oxide Nanoparticle Composites

“…Along the same lines, 139,170 Dey et al reported triazinebased porous polyurethane for immobilization of Pd NPs. 171 However, unlike TP-POP and PC-POP, the triazine-based polymer contained mesopores with sizes between 2 and 20 nm which resulted in an exceptionally broad distribution of Pd NPs (5−20 nm). The authors claim a successful Suzuki− Miyaura cross-coupling reaction, but it is difficult to follow the structure−property relationships with such a catalyst.…”

Oxidase Mimetic Activity of a Metalloporphyrin-Containing Porous Organic Polymer and Its Applications for Colorimetric Detection of Both Ascorbic Acid and Glutathione

“…Porous organic framework materials (POPs), including metal organic framework (MOFs), covalent organic framework, and hydrogen-bonded organic framework, − have been widely explored in gas storage, separation, biosensing, heterogeneous catalysis, and the medical field in the past decade due to their unique structure and performances. − Porphyrin, as a popular organic chromophore, is widely distributed in human heme and plant chlorophyll. It plays important roles in photosynthesis of plants and oxygen transport in human blood .…”

Enhanced Performance of Organic/Inorganic Hybrid Nanomaterials bearing Impregnated [PdL2] Complexes as Counter‐Electrode Catalyst for Dye‐Sensitized Solar Cells

“…Undoubtedly, immobilized systems are very attractive for the catalysis (reduction‐hydrogenation, oxidation, C‐C bond formation reactions etc.). Similar expressions can be said for materials or complexes containing palladium metal and the location of the palladium compounds is to particular importance in the catalyst chemistry . Likewise, the materials or complexes bearing palladium have been used for various purposes in photovoltaic studies …”