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Synthesis 2011(7): 1019-1036  
DOI: 10.1055/s-0030-1258461
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Transition-Metal-Catalyzed Domino Reactions: Efficient One-Pot Regiospecific Synthesis of Highly Functionalized Polysubstituted Furans from Electron-Deficient Alkynes and 2-Yn-1-ols

Hua Caoa,b, Huanfeng Jiang*a, Huawen Huanga
a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. of China
Fax: +86(20)87112906; e-Mail: jianghf@scut.edu.cn;
b School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Guangzhou 510006, P. R. of China
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Publication History

Received 14 December 2010
Publication Date:
03 March 2011 (online)

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Abstract

Based on the reactive behavior of different transition-metal catalysts, three methods for the synthesis of highly functionalized polysubstituted furan derivatives are presented: (i) copper(I) iodide catalyzed regiospecific synthesis of furan aldehydes/ketones from alkynols and diethyl but-2-ynedioate under atmospheric pressure; (ii) nano-Cu2O-catalyzed domino process for the regioselective synthesis of α-carbonylfurans from readily accessible starting materials; (iii) silver-catalyzed one-pot cyclization in toluene at 50 ˚C for the synthesis of furan derivatives. It was notably that all the domino reactions were smooth under mild conditions with commercially available catalysts, and afforded highly functionalized furans in moderate to good yields. As we know, furans derivatives are extremely useful organic molecules used as synthetic building blocks for the synthesis of more elaborate heterocyclic compounds.

Key words

transition-metal-catalyzed domino reaction - functionalized polysubstituted furan - copper(I) iodide - nano-Cu2O - silver(I) acetate

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