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Issue 29, 2018
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Palladium-catalyzed dehydrogenative coupling of cyclic enones with thiophenes: a rapid access to β-heteroarylated cyclic enones

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Abstract

Dehydrogenative coupling of cyclic enones with heteroarenes has been a longstanding challenge because of the competitive ketone dehydrogenation and conjugated addition. Herein, a dehydrogenative coupling reaction of cyclic enones of different sizes with substituted thiophenes to construct β-thienyl cyclic enone compounds through palladium-catalyzed C–H functionalization under mild reaction conditions is reported. Simple substituted thiophenes with different functional groups can be directly introduced into cyclic enones with predominant regioselectivity at the α position of thiophene moieties and excellent functional group tolerance. Further molecular transformations of the coupling products to synthetically useful meta-heteroarylated phenol derivatives have also been demonstrated.

Graphical abstract: Palladium-catalyzed dehydrogenative coupling of cyclic enones with thiophenes: a rapid access to β-heteroarylated cyclic enones

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Publication details

The article was received on 07 Feb 2018, accepted on 12 Mar 2018 and first published on 13 Mar 2018


Article type: Communication
DOI: 10.1039/C8CC01059E
Citation: Chem. Commun., 2018,54, 3668-3671
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    Palladium-catalyzed dehydrogenative coupling of cyclic enones with thiophenes: a rapid access to β-heteroarylated cyclic enones

    Z. Wen, T. Song, Y. Liu and J. Chao, Chem. Commun., 2018, 54, 3668
    DOI: 10.1039/C8CC01059E

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