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Issue 28, 2018
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Copper-catalyzed oxidative cross-dehydrogenative coupling of 2H-chromenes and terminal alkynes

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Abstract

An efficient copper-catalyzed cross-dehydrogenative coupling of 2H-chromenes and terminal alkynes mediated by DDQ has been established. A protic additive, EtOH, proved to be crucial for harmonizing the oxidation with a subsequent alkynylation step by retaining the oxidation state of an oxocarbenium ion in the form of acetal. The CDC reaction exhibits a good substrate scope, with a range of terminal aryl- and alkyl alkynes being well tolerated. The copper-catalyzed alkynylation of 2H-chromene acetals with terminal alkynes was also explored.

Graphical abstract: Copper-catalyzed oxidative cross-dehydrogenative coupling of 2H-chromenes and terminal alkynes

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Publication details

The article was received on 23 Apr 2018, accepted on 24 Jun 2018 and first published on 25 Jun 2018


Article type: Paper
DOI: 10.1039/C8OB00949J
Citation: Org. Biomol. Chem., 2018,16, 5144-5149
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    Copper-catalyzed oxidative cross-dehydrogenative coupling of 2H-chromenes and terminal alkynes

    F. Yang, Y. Li, P. E. Floreancig, X. Li and L. Liu, Org. Biomol. Chem., 2018, 16, 5144
    DOI: 10.1039/C8OB00949J

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