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Issue 38, 2019
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The nickel-catalyzed C3-acylation of 2H-indazoles with aldehydes

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Abstract

A direct coupling of 2H-indazoles’ C3 position and acyl groups has been achieved to produce 3-acyl-2H-indazoles. The Ni(II)-catalyzed acylation might proceed through a radical pathway for the reaction of 2H-indazoles with either aryl or alkyl aldehydes in the presence of the free radical initiator TBHP and additive PivOH. This method provided a superior approach to fulfil the direct C3-acylation of 2H-indazoles with yields up to 91%. And various substituted 2H-indazoles were well tolerated with this method, enriching the diversity of 2H-indazole derivatives. In comparison with previously reported approaches for the C3-acylation of 2H-indazoles, the developed reaction represents a more convenient and economical method directly using aldehydes as the acylation agents.

Graphical abstract: The nickel-catalyzed C3-acylation of 2H-indazoles with aldehydes

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Publication details

The article was received on 08 Aug 2019, accepted on 09 Sep 2019 and first published on 10 Sep 2019


Article type: Paper
DOI: 10.1039/C9OB01749F
Org. Biomol. Chem., 2019,17, 8749-8755

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    The nickel-catalyzed C3-acylation of 2H-indazoles with aldehydes

    Y. Liu, Y. Pan, G. Li, H. Xu and J. Chen, Org. Biomol. Chem., 2019, 17, 8749
    DOI: 10.1039/C9OB01749F

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