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Efficient Synthesis and Structural Analysis of Chiral 4,4'-Biazulene.
Hatakenaka, Ryoji; Nishikawa, Nanami; Mikata, Yuji; Aoyama, Hiroki; Yamashita, Kohsuke; Shiota, Yoshihito; Yoshizawa, Kazunari; Kawasaki, Yuuya; Tomooka, Katsuhiko; Kamijo, Shin; Tani, Fumito; Murafuji, Toshihiro.
Afiliación
  • Hatakenaka R; Graduate School of Sciences and Technology for Innovation, Yamaguchi University, Yamaguchi, 753-8512, Japan.
  • Nishikawa N; Graduate School of Sciences and Technology for Innovation, Yamaguchi University, Yamaguchi, 753-8512, Japan.
  • Mikata Y; Laboratory for Molecular & Functional Design, Department of Engineering, Nara Women's University, Nara, 630-8506, Japan.
  • Aoyama H; Graduate School of Science, Kyushu University, Fukuoka, 819-0395, Japan.
  • Yamashita K; Graduate School of Engineering, Kyushu University, Fukuoka, 819-0395, Japan.
  • Shiota Y; Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan.
  • Yoshizawa K; Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan.
  • Kawasaki Y; Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, Fukuoka, 816-8580, Japan.
  • Tomooka K; Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, Fukuoka, 816-8580, Japan.
  • Kamijo S; Graduate School of Sciences and Technology for Innovation, Yamaguchi University, Yamaguchi, 753-8512, Japan.
  • Tani F; Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka, 819-0395, Japan.
  • Murafuji T; Graduate School of Sciences and Technology for Innovation, Yamaguchi University, Yamaguchi, 753-8512, Japan.
Chemistry ; 30(24): e202400098, 2024 Apr 25.
Article en En | MEDLINE | ID: mdl-38376431
ABSTRACT
4,4'-Biazulene is a potentially attractive key component of an axially chiral biaryl compound, however, its structure and properties have not been clarified owing to the lack of its efficient synthesis. We report a breakthrough in the reliable synthesis of 4,4'-biazulene, which is achieved by the access to azulen-4-ylboronic acid pinacol ester and 4-iodoazulene as novel key synthetic intermediates for the Suzuki-Miyaura cross-coupling reaction. The X-ray crystallographic analysis of 4,4'-biazulene confirmed its axial chirality. The enantiomers of 4,4'-biazulene were successfully resolved by HPLC on the chiral stationary phase column. The kinetic experiments and DFT calculations indicate that the racemization energy barrier of 4,4'-biazulene is comparable to that of 1,1'-binaphthyl.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Alemania