Download PDF
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
Further Information

Publication History

Received 29 December 2007
Publication Date:
07 April 2008 (online)

    Permissions and Reprints All articles of this category

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