tert-BuOK-mediated carbanion-yne intramolecular cyclization: synthesis of 2-substituted 3-benzylbenzofurans |
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| Authors: | Po-Yuan ChenTzu-Pin Wang Keng-Shiang HuangChai-Lin Kao Jui-Chi TsaiEng-Chi Wang |
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| Institution: | a Department of Medicinal & Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan
b School of Chinese Medicine for Post-Baccalaureate, I-Shou University, Kaohsiung 82445, Taiwan |
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| Abstract: | A mild, efficient, and regioselective carbanion-yne intramolecular cyclization mediated by t-BuOK for the synthesis of 2-substituted 3-benzylbenzofurans is developed. It was started from o-iodophenol (1), based on O-alkylation, and the Sonogashira reaction in sequence to produce 2-(2-phenylethynylphenoxy)-1-arylalkanones (5). An intramolecular carbanion-yne 5-exo-dig cyclization reaction of 5, which was mediated by t-BuOK, yielded title benzofurans in good yields. |
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| Keywords: | o-Iodophenol Sonogashira reaction Carbanion-yne intramolecular cyclization 5-exo-dig Cyclization 2-Substituted 3-benzylbenzofurans |
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