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

Organic & Biomolecular Chemistry Pub Date: 2018-11-01 DOI: 10.1039/C8OB02230E

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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