Heterogeneous palladium catalysts are quite useful for synthetic and process chemistry field due to their reusability. We envisioned that DIAION WA30 (WA30, Mitsubishi Chemical Co.), a polystyrene-divinylbenzene based resin possessing a tertiary-amine functions on the aromatic ring, would be a efficient support to develop a functional palladium catalyst due to ligand and partial catalyst poisoning effect of the amino group based on the coordinate nature. 7% Pd/WA30 exhibited a unique chemoselective catalyst activity in hydrogenation. Benzyl alcohols, alkyl benzyl ethers, and silyl ethers were totally tolerant, while aromatic benzyl ethers, N-Cbz groups, nitro groups, alkenes, alkynes, and azides were smoothly hydrgenated. 7% Pd/WA30 could be reused without any decrease in the catalyst activity until at least 5th run. 7% Pd/WA30 also effectively catalyzed Suzuki-Miyaura reaction using chloroarenes as less reactive substrates probably due to the ligand (electron donating) effect of the tertiary-amino group on WA30 to Pd metal. Various aryl chlorides including heteroaryl chlorides were found to be good substrates for the 7% Pd/WA30-catalyzed Suzuki-Miyaura reaction in the presence of Cs2CO3 in DMA. It is noteworthy that Pd metal leaching into the solvent was never detected by ICP-AES. In this symposium, the details of the preparation method of Pd/WA30 and its application to the chemoselective hydrogenation and Suzuki-Miyaura reaction.

Anion exchange resin supported –palladium catalyst for chemoselective hydrogenation and Suzuki-Miyaura reaction using aryl chlorides

256th National Meeting (2018)

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