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

Author:

Hatakenaka Ryoji1,Nishikawa Nanami1,Mikata Yuji2ORCID,Aoyama Hiroki3,Yamashita Kohsuke4,Shiota Yoshihito5ORCID,Yoshizawa Kazunari5ORCID,Kawasaki Yuuya6ORCID,Tomooka Katsuhiko6ORCID,Kamijo Shin1ORCID,Tani Fumito5ORCID,Murafuji Toshihiro1ORCID

Affiliation:

1. Graduate School of Sciences and Technology for Innovation Yamaguchi University Yamaguchi 753-8512 Japan

2. Laboratory for Molecular & Functional Design Department of Engineering Nara Women's University Nara 630-8506 Japan

3. Graduate School of Science Kyushu University Fukuoka 819-0395 Japan

4. Graduate School of Engineering Kyushu University Fukuoka 819-0395 Japan

5. Institute for Materials Chemistry and Engineering Kyushu University 744 Motooka, Nishi-ku Fukuoka 819-0395 Japan

6. Institute for Materials Chemistry and Engineering Kyushu University 6-1 Kasuga-koen Kasuga Fukuoka 816-8580 Japan

Abstract

Abstract4,4′‐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.

Publisher

Wiley

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