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One‐Pot Synthesis of Indoles from Aniline and α,β‐Ynones through an Iodine‐Mediated Transition‐Metal‐Free Tandem aza‐Michael addition/C−H Functionalization

One‐Pot Synthesis of Indoles from Aniline and α,β‐Ynones through an Iodine‐Mediated... An efficient iodine‐mediated aza‐Michael addition/C−H functionalization procedure for the synthesis of indoles was achieved in one pot. By simple aza‐Michael addition between anilines and α,β‐ynones, a series of N‐aryl enaminones intermediate was generated, followed by iodine‐mediated C−H functionalization, a wide variety of indole derivatives were obtained in moderate to excellent yields under transition‐metal‐free conditions. Control experiments and in situ ESI‐MS analysis indicated the reaction occurred via a radical mechanism. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

One‐Pot Synthesis of Indoles from Aniline and α,β‐Ynones through an Iodine‐Mediated Transition‐Metal‐Free Tandem aza‐Michael addition/C−H Functionalization

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References (42)

Publisher
Wiley
Copyright
© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201900152
Publisher site
See Article on Publisher Site

Abstract

An efficient iodine‐mediated aza‐Michael addition/C−H functionalization procedure for the synthesis of indoles was achieved in one pot. By simple aza‐Michael addition between anilines and α,β‐ynones, a series of N‐aryl enaminones intermediate was generated, followed by iodine‐mediated C−H functionalization, a wide variety of indole derivatives were obtained in moderate to excellent yields under transition‐metal‐free conditions. Control experiments and in situ ESI‐MS analysis indicated the reaction occurred via a radical mechanism.

Journal

Asian Journal of Organic ChemistryWiley

Published: Apr 1, 2019

Keywords: ; ; ; ;

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