Sawama Yoshinari, Asai Shota, Kawajiri Takahiro, Monguchi Yasunari, Sajiki Hironao
Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigakunishi, Gifu 501-1196 (Japan).
Chemistry. 2015 Jan 26;21(5):2222-9. doi: 10.1002/chem.201405558. Epub 2014 Dec 2.
Biaryl and heterobiaryl compounds are important frameworks across a range of fields including pharmaceutical and functional material chemistries. We have accomplished the efficient synthesis of various naphthalene-linked arenes and heteroarenes as biaryls and heterobiaryls by the FeCl3 -catalyzed Friedel-Crafts reactions accompanied by the ring-opening of the 1,4-epoxy moiety of 1,4-epoxy-1,4-dihydronaphthalenes. Especially, it is noteworthy that 1-silylated substrates were regioselectively transformed to the 3-aryl-1-silylnaphthalenes and the double Friedel-Crafts reactions using thiophene derivatives could directly produce the corresponding bis-naphthlated thiophene derivatives.
联芳基和杂联芳基化合物是包括药物化学和功能材料化学在内的一系列领域中的重要骨架。我们通过FeCl₃催化的傅克反应，伴随着1,4 - 环氧 - 1,4 - 二氢萘的1,4 - 环氧部分的开环，实现了各种萘连接的芳烃和杂芳烃作为联芳基和杂联芳基的高效合成。特别值得注意的是，1 - 硅烷基化底物区域选择性地转化为3 - 芳基 - 1 - 硅烷基萘，并且使用噻吩衍生物的双傅克反应可以直接产生相应的双萘基化噻吩衍生物。
