Peripherally Arylated 2,8-Diazaperylenes from Anthracene Diimide: Synthesis and Oxidative Annulation
Peripherally Arylated 2,8-Diazaperylenes from Anthracene Diimide: Synthesis and Oxidative Annulation
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蒽二酰亚胺外围芳基化 2,8-二氮苝：合成和氧化成环
DOI：
10.1021/acs.orglett.1c00253
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发表时间：
2021
期刊：
影响因子：
5.2
通讯作者：
Miyake Yoshihiro
中科院分区：
文献类型：
--
作者：
Sakurai Takahiro;Nakazato Takumi;Shinokubo Hiroshi;Miyake Yoshihiro
在锌粉和特戊酸酐存在下，蒽二酰亚胺还原芳构化合成了1，3，7，9-四特戊氧基-2，8-二氮杂萘。通过镍催化的与芳基硼酸的交叉偶联反应，新戊氧基容易地转化为芳基。氮原子的引入赋予了对二萘嵌苯骨架的酸响应性，导致其物理性质的显著变化。二氮杂环戊二烯核的bay位与外围芳基氧化成环，得到2，10-二氮杂二苯并冠烯，产率较高
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