Design and Synthesis of Functionalized NHC Ligands for Transition Metal-Catalyzed Arylation Reactions

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  • Kuriyama Masami
    Graduate School of Biomedical Sciences, Nagasaki University
  • Shirai Ryuichi
    Faculty of Pharmaceutical Sciences, Doshisha Women's College of Liberal Arts
  • Onomura Osamu
    Graduate School of Biomedical Sciences, Nagasaki University

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Other Title
  • 官能基化されたNHC配位子の開発と触媒的アリール化反応へ適用
  • 官能基化されたNHC配位子の開発と触媒的アリール化反応への適用
  • カンノウキカ サレタ NHC ハイイシ ノ カイハツ ト ショクバイテキ アリールカ ハンノウ エ ノ テキヨウ

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Abstract

Effective ligand design for metal-catalyzed reactions is highly important to control catalyst performance. Especially, readily-synthesized and easy-to-handle ligands with the ability to realize high reaction efficiency and substrate tolerance have been still desired. We have developed novel N-heterocyclic carbene ligands on the basis of the concept of hemilabile coordination, whose precursors were prepared in short steps and obtained as crystalline solids stable enough to handle and store under the air. The thioether-imidazolinium chlorides achieved excellent catalyst activity in the palladium-catalyzed arylation of aldehydes. On the other hand, the ether-imidazolium carbenes were found to be highly effective in the Suzuki-Miyaura reaction. In both cases, remarkable substrate tolerance was observed, which realized the efficient transformation of heterocycle-containing compounds.

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