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Steric and electronic effects of arsa-Buchwald ligands on Suzuki-Miyaura coupling reaction.
Sumida, Akifumi; Ogawa, Kenta; Imoto, Hiroaki; Naka, Kensuke.
Afiliación
  • Sumida A; Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Goshokaido-cho, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. himoto@kit.ac.jp.
  • Ogawa K; Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Goshokaido-cho, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. himoto@kit.ac.jp.
  • Imoto H; Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Goshokaido-cho, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. himoto@kit.ac.jp.
  • Naka K; Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Goshokaido-cho, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan. himoto@kit.ac.jp.
Dalton Trans ; 52(9): 2838-2844, 2023 Feb 28.
Article en En | MEDLINE | ID: mdl-36756968
The Suzuki-Miyaura coupling (SMC) reaction is one of the most commonly used cross-coupling reactions. Bulky biaryldialkyl monophosphine ligands, i.e., Buchwald ligands, are beneficial for the SMC reaction. We recently developed a synthetic procedure for arsa-Buchwald ligands, arsenic analogs of Buchwald ligands, and found that these ligands are effective for sterically hindered substrates because of facilitating the transmetalation step owing to the longer arsenic-palladium bond. However, the relationship between the structure and steric/electronic properties of the arsa-Buchwald ligands has not yet been studied in detail. In this study, a series of arsa-Buchwald ligands with various alkyl substituents were synthesized. The cyclopentyl group afforded the highest catalytic activity for the SMC reaction, particularly with sterically hindered substrates. Furthermore, the steric/electronic properties of the arsa-Buchwald ligands were computationally analyzed.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Dalton Trans Asunto de la revista: QUIMICA Año: 2023 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Reino Unido
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Dalton Trans Asunto de la revista: QUIMICA Año: 2023 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Reino Unido