Sakurai Takahiro, Nakazato Takumi, Shinokubo Hiroshi, Miyake Yoshihiro
Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya 464-8603, Japan.
Org Lett. 2021 Mar 19;23(6):2099-2103. doi: 10.1021/acs.orglett.1c00253. Epub 2021 Mar 10.
We have synthesized 1,3,7,9-tetrapivaloxy-2,8-diazaperylene through reductive aromatization of anthracene diimide in the presence of zinc powder and pivalic anhydride. The pivaloxy groups were readily converted to aryl groups through nickel-catalyzed cross-coupling reaction with arylboronic acids. Introduction of the nitrogen atoms imparts acid responsiveness to the perylene skeleton, resulting significant changes in its photophysical properties. Oxidative annulation of the peripheral aryl groups with bay positions of the diazaperylene core provided 2,10-diazadibenzocoronenes in good yields.
我们通过在锌粉和新戊酸酐存在下对蒽二亚胺进行还原芳构化反应，合成了1,3,7,9-四新戊氧基-2,8-二氮杂苝。新戊氧基通过与芳基硼酸的镍催化交叉偶联反应很容易转化为芳基。氮原子的引入赋予了苝骨架酸响应性，导致其光物理性质发生显著变化。外围芳基与二氮杂苝核心的湾区位置进行氧化环合反应，以良好的产率得到了2,10-二氮杂二苯并蔻。
