Development of <i>N</i>-Heterocyclic Carbene (NHC)–palladium Complex Catalyst and Immobilized NHC–palladium Complex Catalyst

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  • <i>N</i>-ヘテロ環状カルベン–パラジウム錯体およびその固定化触媒の開発
  • Development of N-Heterocyclic Carbene (NHC)-palladium Complex Catalyst and Immobilized NHC-palladium Complex Catalyst

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Abstract

<p>Conventional methods for preparing catalysts for the immobilization of N-heterocyclic carbenes (NHC)-metal complex use the substituent on the nitrogen as the immobilization site with the support, and the bulkiness of the substituent on the nitrogen, which is a characteristic of NHC ligands, cannot be fully utilized. In this study, we focused on the backbone carbon of NHC and devised a new catalyst design that uses backbone carbon as the binding point with the support. First, various silyl groups were introduced into the backbone carbon of IPr (1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), and Si–IPr–Pd complex catalysts were synthesized. The electronic properties of the introduced silyl groups were investigated, and it was confirmed that the introduction of electron-donating silyl groups enhanced the catalytic activity in C–N coupling reaction. Next, we applied this knowledge to the immobilization of Si–IPr–Pd complex catalyst with a dimethylchlorosilyl group on polystyrene resin to develop a new immobilized NHC–Pd complex catalyst with an electron-donating oxosilyl group as the binding point to the support. Finally, the catalytic performance was evaluated in the C–N coupling reaction, and the catalyst exhibited high activity, and the amount of residual Pd in the filtrate after the reaction was below the detection limit (<1 ppm).</p>

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