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2-(1-Methylhydrazinyl)pyridine as a reductively removable directing group in a cobalt-catalyzed C(sp2)–H bond alkenylation/annulation cascade

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Abstract

We describe a new application of 2-(1-methylhydrazinyl)pyridine as a bidentate directing group to directing cobalt-catalyzed C(sp2)–H alkenylation/annulation of the corresponding benzoic hydrazides to form an isoquinoline backbone, via reacting with a terminal or internal alkyne followed by annulation. The reaction shows a broad substrate scope with the products obtained in good to excellent yields and high regioselectivity. Moreover, the directing group can be reductively removed in one step under mild conditions.

Graphical abstract: 2-(1-Methylhydrazinyl)pyridine as a reductively removable directing group in a cobalt-catalyzed C(sp2)–H bond alkenylation/annulation cascade

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Publication details

The article was received on 06 Nov 2017, accepted on 23 Nov 2017 and first published on 24 Nov 2017


Article type: Communication
DOI: 10.1039/C7CC08533H
Citation: Chem. Commun., 2018, Advance Article
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    2-(1-Methylhydrazinyl)pyridine as a reductively removable directing group in a cobalt-catalyzed C(sp2)–H bond alkenylation/annulation cascade

    S. Zhai, S. Qiu, X. Chen, J. Wu, H. Zhao, C. Tao, Y. Li, B. Cheng, H. Wang and H. Zhai, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C7CC08533H

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