Rhodium‐Catalyzed Intramolecular Hydroarylation of 1‐Halo‐1‐alkynes: Regioselective Synthesis of Semihydrogenated Aromatic Heterocycles |
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| Authors: | Hirohiko Murase Kousuke Senda Masato Senoo Prof?Dr Takeshi Hata Prof?Dr Hirokazu Urabe |
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| Institution: | Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259‐B‐59 Nagatsuta‐cho, Midori‐ku, Yokohama, Kanagawa 226‐8501 (Japan), Fax: (+81)?(0)45‐924‐5849 |
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| Abstract: | The regioselective intramolecular hydroarylation of (3‐halo‐2‐propynyl)anilines, (3‐halo‐2‐propynyl) aryl ethers, or (4‐halo‐3‐butynyl) aryl ethers was efficiently catalyzed by Rh2(OCOCF3)4 to give semihydrogenated aromatic heterocycles, such as 4‐halo‐1,2‐dihydroquinolines, 4‐halo‐3‐chromenes, or 4‐(halomethylene)chromans, in good to excellent yields. Some synthetic applications taking advantage of the halo‐substituents of the products are also illustrated. |
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| Keywords: | chromene dihydroquinolines heterocycles hydroarylation rhodium |
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