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Issue 44, 2016
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Chemoselective reduction of quinols as an alternative to Sonogashira coupling: synthesis of polysubstituted benzofurans

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Abstract

An efficient synthetic approach to polysubstituted benzofurans is described, using 2-methoxyquinone as a benzofuran backbone. Nucleophilic addition of terminal alkynes to 2-methoxy-1,4-benzoquinone afforded the corresponding quinols containing an alkyne unit, which were converted to phenols via mild Zn-mediated reduction. After proper protection of the free phenolic OH, 5-endo-dig iodocyclization allowed facile access to a number of 3-iodobenzofurans. In addition, it was demonstrated for the first time that o-methoxyarylalkynes underwent intramolecular hydroalkoxylation under the influence of AgOTf furnishing the corresponding benzofurans.

Graphical abstract: Chemoselective reduction of quinols as an alternative to Sonogashira coupling: synthesis of polysubstituted benzofurans

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Publication details

The article was received on 03 Sep 2016, accepted on 12 Oct 2016 and first published on 13 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB01941B
Citation: Org. Biomol. Chem., 2016,14, 10454-10472
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    Chemoselective reduction of quinols as an alternative to Sonogashira coupling: synthesis of polysubstituted benzofurans

    Y. Jung and I. Kim, Org. Biomol. Chem., 2016, 14, 10454
    DOI: 10.1039/C6OB01941B

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