Efficient Synthesis of Monosubstituted 3-Alkynylfurans via Suzuki Coupling

Xiaobao Yang; Li Zhu; Yuedong Zhou; Zhong Li; Hongbin Zhai

doi:10.1055/s-2008-1072576

PAPER

Efficient Synthesis of Monosubstituted 3-Alkynylfurans via Suzuki Coupling

Xiaobao Yang^a,b, Li Zhu^c,b, Yuedong Zhou^d,b, Zhong Li*^a, Hongbin Zhai*^b
^a School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. of China
^b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: zhaih@mail.sioc.ac.cn;
^c Department of Chemistry, Shanghai University, Shanghai 200436, P. R. of China
^d Hefei National Laboratory for Physical Science at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. of China

Abstract

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Abstract

A convenient synthesis of monosubstituted 3-alkynylfurans by Suzuki coupling reaction of 3-furanylboronic acid with substituted acetylene bromides is described. The internal alkyne products were attainable in 50-89% yields from substrates free of relatively acidic protons. Our protocol is expected to find applications in the synthesis of structurally related natural products.

Key words

Suzuki coupling - monosubstituted 3-alkynylfurans - 3-furanylboronic acid - bromoalkynes

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