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Palladium-Catalyzed Cross-Coupling Reactions of 1,2-Diiodoalkenes with Terminal Alkynes: Selective Synthesis of Unsymmetrical Buta-1,3-diynes and 2-Ethynylbenzofurans

Yun Liang, Li-Ming Tao, Yue-Hu Zhang, Jin-Heng Li*

*Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China, Email: jhlihunnu.edu.cn

Y. Liang, L.-M. Tao, Y.-H. Zhang, J.-H. Li, Synthesis, 2008, 3988-3994.

DOI: 10.1055/s-0028-1083251


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Abstract

In the presence of palladium(II) acetate and copper(I) iodide, unsymmetrical buta-1,3-diynes were selectively obtained from the reaction of (E)-1,2-diiodoalkenes with terminal alkynes in moderate to good yields at room temperature. Using the same conditions, the coupling of 2-ethynylphenol with (E)-1,2-diiodoalkenes followed by a cyclization at 100C gives ethynylbenzofurans.

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Key Words

palladium(II) acetate, copper(I) iodide, Sonogashira Coupling, (E)-1,2-diiodoalkene, terminal alkynes, diynes, buta-1,3-diyne, 2-ethynylbenzofuran, benzofurans


ID: J66-Y2008-3820