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Issue 87, 2012
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Copper-mediated oxidative direct C–C (hetero)aromatic cross-coupling

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Abstract

Some new types of copper-mediated intermolecular oxidative direct C–C (hetero)aromatic cross-couplings are described. A combination of the simple CuCl2 salt and molecular oxygen allows 1,3-azoles to couple with terminal alkynes directly to form the corresponding heteroarylacetylenes. This direct version of Sonogashira-type coupling can be applied to the reaction with polyfluoroarenes. A copper acetate complex enables direct biaryl coupling between 2-arylazines and 1,3-azoles even in the absence of any palladium catalysts. Moreover, the Cu-based protocol can be extended to the coupling with indoles and pyrroles, in which a catalytic variant is also possible by using an ideal co-oxidant, atmospheric oxygen. On the other hand, a copper-promoted annulative direct coupling of o-alkynylphenols and -anilines with 1,3-azoles can provide a unique dehydrogenative approach to C3-azolylbenzoheteroles from nonhalogenated and nonmetalated starting materials. In addition, a related N-azolylindole synthesis from similar substrates is also disclosed.

Graphical abstract: Copper-mediated oxidative direct C–C (hetero)aromatic cross-coupling

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Publication details

The article was received on 29 Jun 2012, accepted on 21 Aug 2012 and first published on 18 Sep 2012


Article type: Feature Article
DOI: 10.1039/C2CC34659A
Chem. Commun., 2012,48, 10704-10714

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    Copper-mediated oxidative direct C–C (hetero)aromatic cross-coupling

    K. Hirano and M. Miura, Chem. Commun., 2012, 48, 10704
    DOI: 10.1039/C2CC34659A

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