Visible‐Light‐Enhanced Suzuki–Miyaura Reactions of Aryl Chlorides in Water with Pd NPs Supported on a Conjugated Nanoporous Polycarbazole

Abstract

The visible‐light‐enhanced catalytic activation of aryl chlorides for Suzuki–Miyaura cross‐coupling (SMC) reactions is highly challenging because of the strength of the C−Cl bond. In this work, palladium nanoparticles (Pd NPs) were grown on a conjugated nanoporous polycarbazole (CNP), named Pd/CNP. The hybrid material Pd/CNP could catalyze the SMC reactions of aryl chlorides with arylboronic acids in water under blue LED irradiation at room temperature with high efficiency. This protocol exhibited good functional group tolerance and the catalyst could be recycled without significant loss of its catalytic activity. CNP not only provided photogenerated electrons to enrich the electron density of the Pd NPs but also generated holes for the activation of the arylboronic acids.

Synthesis of a Pyrazole-Based Microporous Organic Polymer for High-Performance CO2 Capture and Alkyne Carboxylation

“…Characterization techniques were performed as detailed in our previous publication. 44 2.2. Synthesis of MOP-PZ.…”

“…The CN and NH groups of pyrazole can potentially anchor metal ions or stabilize metal nanoparticles (NPs). 25,26,43,44 The NH group of pyrazole could enhance the adsorption of CO 2 . 45−50 Metal NPs supported on MOPs (M-MOPs) displayed high catalytic activity toward the hydroformylation of olefins, 51 the Suzuki−Miyaura coupling reaction, 33,41 hydrogenation of CO 2 , 26 and reduction of nitroarenes.…”

“…Aromatic hydrocarbons, − arylamine, 1,10-phenanthroline, triphenylphosphane, thiophene, furan, pyrrole, , porphyrin, benzothiadiazole, and carbazole − can be polymerized into functional microporous organic polymers via the Scholl coupling reaction, ,,, “knitting” with formaldehyde dimethyl acetal (FDA), ,,,,,,, or via the solvent knitting method. ,,,,, We are unaware of previous reports of pyrazole-based MOPs. The CN and NH groups of pyrazole can potentially anchor metal ions or stabilize metal nanoparticles (NPs). ,,, The NH group of pyrazole could enhance the adsorption of CO 2 . − Metal NPs supported on MOPs (M-MOPs) displayed high catalytic activity toward the hydroformylation of olefins, the Suzuki–Miyaura coupling reaction, , hydrogenation of CO 2 , and reduction of nitroarenes. ,, To date, the utilization of M-MOPs as heterogeneous catalysts for carboxylation of alkyne with CO 2 remains unexplored. In this work, we selected 3,5-diphenyl-1 H -pyrazole as a building unit to construct a porous framework using a simple one-pot Scholl coupling polymerization.…”

Construction of a (NNN)Ru-Incorporated Porous Organic Polymer with High Catalytic Activity for β-Alkylation of Secondary Alcohols with Primary Alcohols

“…The analytical instruments employed in this work are as described in our previous article [57,64,65], unless otherwise noted. 1 H and 13 C NMR spectra were recorded at ambient temperature on a Varian UNITY plus-400 spectrometer.…”

Pd–Co Nanoparticles Supported on Calcined Mg–Fe Hydrotalcites for the Suzuki–Miyaura Reaction in Water with High Turnover Numbers

“…By contrast, a heterogeneous Pd catalyst could obviate these limitations and open up a valuable alternative technology in such processes [13][14][15][16][17]. In recent years, palladium nanoparticles (NPs) supported by various substrates, such as active carbon materials [18,19], silica [20][21][22], polymers [23,24], inorganic mineral [25,26], metal oxides [27][28][29], and covalent organic frameworks (COFs) [30,31] have been designed and applied for the Suzuki-Miyaura reaction. However, these methods usually require high catalyst loadings (from 0.021 to 1 mol % Pd), high-reaction temperatures, and long reaction times.…”