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. 2013 Apr;69(13):2701-2713.
doi: 10.1016/j.tet.2013.02.003.

Efficient Microwave-assisted One-pot Three-component Synthesis of 2,3-Disubstituted Benzofurans under Sonogashira Conditions

Nataliya A Markina  1 , Yu Chen, Richard C Larock
Affiliations

Efficient Microwave-assisted One-pot Three-component Synthesis of 2,3-Disubstituted Benzofurans under Sonogashira Conditions

Nataliya A Markina et al. Tetrahedron. 2013 Apr.

Abstract

An efficient one-pot method for the synthesis of 2,3-disubstituted benzo[b]furans from commercially available 2-iodophenols, terminal acetylenes and aryl iodides has been developed utilizing Sonogashira reaction conditions. After an initial Sonogashira coupling of the 2-iodophenol with the terminal alkyne, cyclization involving the aryl iodide provides the 2,3-disubstituted benzo[b]furan in good to excellent yields. The use of microwave irradiation shortens the reaction times and minimizes the side products. This methodology is especially useful for the construction of libraries of highly substituted benzo[b]furans and their analogues.

Keywords: Sonogashira coupling; benzofuran; microwave; three-component reaction.

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Figures

Scheme 1
Scheme 1
A one-pot approach to benzofurans using MeMgCl
Scheme 2
Scheme 2
An alternative route employing 4-ethynylbenzonitrile
Scheme 3
Scheme 3
Synthesis of benzofurans from iodophenols, alkynes and alkenes
Scheme 4
Scheme 4
Pd-catalyzed diversification
See this image and copyright information in PMC

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