Palladium-catalyzed Sonogashira coupling reaction followed by isomerization and cyclization |
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Authors: | Chan Sik Cho |
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Affiliation: | Research Institute of Industrial Technology, Kyungpook National University, Bukku, Daegu 702-701, Republic of Korea |
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Abstract: | 2-Iodoaniline reacts with terminal acetylenic carbinols in THF at 80 °C in the presence of a catalytic amount of PdCl2(PPh3)2 and CuI along with aqueous tetrabutylammonium hydroxide to afford the corresponding 2-arylquinolines in good yields. The catalytic pathway seems to be proceeded via a sequence involving initial Sonogashira coupling between 2-iodoaniline and terminal acetylenic carbinols to form coupled acetylenic carbinols, isomerization of coupled acetylenic carbinols to α,β-unsaturated ketones, and cyclodehydration. |
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Keywords: | Cyclization Isomerization Palladium catalyst Quinolines Sonogashira coupling Tetrabutylammonium hydroxide |
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