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Issue 44, 2018
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Accessing 4-oxy-substituted isoquinolinones via C–H activation and regioselective migratory insertion with electronically biased ynol ethers

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Abstract

The rhodium-catalyzed C–H activation and annulation with ynol ethers to directly provide 4-oxy substituted isoquinolinones is reported. The polarized nature of ynol ethers provides an electronic bias for controlling the regioselectivity of the migratory insertion process. While the highly reactive nature of ynol ethers presents a challenge, mild conditions were found to provide product in moderate to good yield. Utility was demonstrated by application in the synthesis of a prolyl-4-hydroxylase inhibitor framework.

Graphical abstract: Accessing 4-oxy-substituted isoquinolinones via C–H activation and regioselective migratory insertion with electronically biased ynol ethers

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Publication details

The article was received on 08 Aug 2018, accepted on 24 Oct 2018 and first published on 24 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02622J
Citation: Org. Biomol. Chem., 2018,16, 8639-8646
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    Accessing 4-oxy-substituted isoquinolinones via C–H activation and regioselective migratory insertion with electronically biased ynol ethers

    B. L. Coles-Taylor, M. S. McCallum, J. S. Lee and B. W. Michel, Org. Biomol. Chem., 2018, 16, 8639
    DOI: 10.1039/C8OB02622J

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