Palladium Nanoparticles Supported on Poly(N-vinylpyrrolidone)-Grafted Silica as an Efficient Catalyst for Copper-Free Sonogashira and Suzuki Cross-Coupling Reactions

Abstract

Palladium catalyst based on polyvinylpyrrolidone-silica hybrid support was prepared and exhibited excellent activity and stability in copper, amine and phosphine-free Sonogashira-Hagihara and Suzuki-Miyaura cross-coupling reactions. The polymeric catalyst was applied efficiently in the coupling reactions of chloro (as well as iodo) and bromoarenes. Elemental analysis of Pd by inductively coupled plasma (ICP) and hot filtration test revealed low leaching of the metal into solution from the supported system. The catalyst could be reused many times in repeated cycles without significant decline in its activity. ]]>

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

“…This catalyst was recovered by filtration and reused in six consecutive runs with only a slight decrease on the activity, ICP-AES analysis of the recovered catalyst showing a negligible leaching of the metal. In addition, the use of polyvinylpyrrolidine-silica hybrid as support for PdNPs 39 were used as catalyst in the reaction between aromatic iodides and bromides, leading to the corresponding products in good yields ( Figure 14) [78]. The use of aryl chlorides containing electron-donor groups as substituents needed the presence of TBAB (5 mol%) affording the expected products in low yields.…”

Nano tetraimine Pd(0) complex as an efficient catalyst for phosphine‐free Suzuki reaction in water and copper‐free Sonogashira reaction under aerobic conditions

“…To catalyse a large variety of carbon–carbon bond forming reactions, palladium is one of the most essential transition metals which is commonly used . Various kinds of cross‐coupling reactions have been investigated; among them coupling reactions such as the Heck–Mizoroki reaction, the Suzuki reaction, the Sonogashira reaction, the Kumada reaction, the Negishi reaction and the Stille reaction are interesting examples of C;C bond formation…”

Advances in Organic and Organic-Inorganic Hybrid Polymeric Supports for Catalytic Applications

“…The application of Pd nanoparticles supported on poly(N-vinylpyrrolidone)-grafted silica as heterogeneous catalysts for Sonogashira and Suzuki coupling reactions was also reported [78]. In detail, catalyst 134 was obtained by treatment of poly(N-vinylpyrrolidone)-grafted silica 133 with Recently, triphenylphosphine ligand and palladium nanoparticles were immobilized in situ in a polymer synthesized by palladium catalysed Suzuki-Miyaura reaction between tris(4-bromophenyl)amine and benzene-1,4-diboronic acid, to which tris(4-chlorophenyl) phosphine participated [77].…”

“…Similar to the Sonogashira reaction, aryl chlorides gave the coupling products in the presence of TBAB. The recycling experiments for the reaction of phenylboronic acid The application of Pd nanoparticles supported on poly(N-vinylpyrrolidone)-grafted silica as heterogeneous catalysts for Sonogashira and Suzuki coupling reactions was also reported [78]. In detail, catalyst 134 was obtained by treatment of poly(N-vinylpyrrolidone)-grafted silica 133 with PdCl 2 in DMF (Scheme 48).…”