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Synthesis 2008(11): 1729-1732  
DOI: 10.1055/s-2008-1072576
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of Monosubstituted 3-Alkynylfurans via Suzuki Coupling

Xiaobao Yanga,b, Li Zhuc,b, Yuedong Zhoud,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
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Publikationsverlauf

Received 29 December 2007
Publikationsdatum:
07. April 2008 (online)

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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