Efficient Synthesis and Structural Analysis of Chiral 4,4′-Biazulene

Ryoji Hatakenaka, Nanami Nishikawa, Yuji Mikata, Hiroki Aoyama, Kohsuke Yamashita, Yoshihito Shiota, Kazunari Yoshizawa, Yuuya Kawasaki, Katsuhiko Tomooka, Shin Kamijo, Fumito Tani, Toshihiro Murafuji

研究成果: ジャーナルへの寄稿学術誌査読

抄録

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.

本文言語英語
論文番号e202400098
ジャーナルChemistry - A European Journal
30
24
DOI
出版ステータス出版済み - 4月 25 2024

!!!All Science Journal Classification (ASJC) codes

  • 触媒
  • 化学一般
  • 有機化学

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