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I2-Triggered N–O cleavage of ketoxime acetates for the synthesis of 3-(4-pyridyl)indoles

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Abstract

A facile and complementary [3 + 2 + 1] annulation of aryl ketoxime acetates and 3-formylindoles to give pyridine derivatives is reported. The condensation reaction demonstrated that I2 was capable of triggering N–O bond cleavage of ketoxime acetates to generate iminyl radicals via a single electron transfer pathway. This direct and operationally simple protocol provides a fundamental platform to synthesize 3-(4-pyridyl)indoles with high functional group compatibility and high regioselectivity.

Graphical abstract: I2-Triggered N–O cleavage of ketoxime acetates for the synthesis of 3-(4-pyridyl)indoles

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Publication details

The article was received on 10 Sep 2018, accepted on 01 Nov 2018 and first published on 01 Nov 2018


Article type: Paper
DOI: 10.1039/C8OB02230E
Citation: Org. Biomol. Chem., 2018, Advance Article
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    I2-Triggered N–O cleavage of ketoxime acetates for the synthesis of 3-(4-pyridyl)indoles

    Q. Gao, Y. Wang, Q. Wang, Y. Zhu, Z. Liu and J. Zhang, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02230E

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