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Synthesis 2008(24): 3988-3994  
DOI: 10.1055/s-0028-1083251
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Yun Lianga, Li-Ming Taoa,b, Yue-Hua Zhanga, Jin-Heng Li*a
a Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China
Fax: +86(731)8872101; e-Mail: jhli@hunnu.edu.cn;
b Department of Chemistry and Life Science, Xiangnan University, Chenzhou 423000, P. R. of China
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Publication History

Received 30 June 2008
Publication Date:
01 December 2008 (online)

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Abstract

(E)-1,2-Diiodoalkenes were found to be effective building blocks for the preparation of unsymmetrical buta-1,3-diynes and 2-ethynylbenzofurans. In the presence of palladium(II) acetate and copper(I) iodide, unsymmetrical buta-1,3-diynes were selectively obtained in moderate to good yields. Moreover, 2-ethynylbenzofurans were obtained in one pot from the reaction of 2-ethynylphenol with (E)-1,2-diiodoalkenes, palladium(II) acetate, and copper(I) iodide by simple heating.

Key words

palladium(II) acetate - copper(I) iodide - (E)-1,2-diiodoalkene - terminal alkyne - buta-1,3-diyne - 2-ethynylbenzofuran