Biaryl Synthesis by Ring‐Opening Friedel–Crafts Arylation of 1,4‐Epoxy‐1,4‐dihydronaphthalenes Catalyzed by Iron Trichloride |
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Authors: | Dr Yoshinari Sawama Shota Asai Takahiro Kawajiri Dr Yasunari Monguchi Prof Dr Hironao Sajiki |
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Institution: | Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1‐25‐4 Daigakunishi, Gifu 501‐1196 (Japan) |
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Abstract: | 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. |
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Keywords: | arenes biaryls Friedel– Crafts reaction iron catalyst ring‐opening reaction |
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