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Chemistry. 2015 Oct 26;21(44):15529-33. doi: 10.1002/chem.201503643. Epub 2015 Sep 25.

Cobalt(III)-Catalyzed Dehydrative [4+2] Annulation of Oxime with Alkyne by C-H and N-OH Activation.

Chemistry (Weinheim an der Bergstrasse, Germany)

Malay Sen, Deepti Kalsi, Basker Sundararaju

Affiliations

  1. Fine Chemical Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur (India).
  2. Fine Chemical Laboratory, Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur (India). [email protected].

PMID: 26407181 DOI: 10.1002/chem.201503643

Abstract

Efficient, scalable cobalt-catalyzed redox-neutral [4+2] annulation of readily available oximes and alkyne is reported. The developed synthetic methodology is widely applicable and tolerates various functional groups including heterocycles. A stable Cp*Co(III) neutral complex is employed as the catalyst for this redox-neutral [4+2] annulation reaction, which progresses smoothly by way of a reversible cyclometallation without any external oxidizing agent, and produces only water as the side product.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: CH activation; annulation; cobalt; heterocycles; isoquinoline

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