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-Hua Zhang; Jin-Heng Li

doi:10.1055/s-0028-1083251

PAPER

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^a, Li-Ming Tao^a,b, Yue-Hua Zhang^a, 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

Abstract

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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

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