10. Indoles

  1. John A. Joule1 and
  2. Keith Mills2

Published Online: 6 AUG 2012

DOI: 10.1002/9781118380208.ch10

Heterocyclic Chemistry at a Glance, Second Edition

Heterocyclic Chemistry at a Glance, Second Edition

How to Cite

Joule, J. A. and Mills, K. (2012) Indoles, in Heterocyclic Chemistry at a Glance, Second Edition, John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/9781118380208.ch10

Author Information

  1. 1

    The School of Chemistry, The University of Manchester, UK

  2. 2

    Independent Consultant, UK

Publication History

  1. Published Online: 6 AUG 2012
  2. Published Print: 4 SEP 2012

ISBN Information

Print ISBN: 9780470971222

Online ISBN: 9781118380208



  • indoles;
  • electrophilic substitution at carbon;
  • sulfur substituents, via electrophilic substitution;
  • electrophilic substitutions of indoles, widely used;
  • indole alkylation with α, β-unsaturated ketones;
  • N-benzoylindole and N-methylindole, via indolyl anion;
  • N-phenylsulfonylindole and N-Boc-indole, via anion;
  • indole N-arylation using palladium/copper catalysis;
  • indoles, and transition metal-catalysed cross-coupling;
  • indoles' electron, side-chain substituent reactivity


This chapter contains sections titled:

  • Electrophilic substitution at carbon

  • N-Deprotonation and N-metallated indoles

  • C-Metallated indoles

  • Palladium(0)-catalysed reactions

  • Oxidation and reduction

  • Pericyclic reactions

  • Reactivity of side-chain substituents

  • Oxygen substituents

  • Ring synthesis – disconnections

  • Synthesis of indoles from arylhydrazones

  • Synthesis of indoles from ortho-nitrotoluenes

  • Synthesis of indoles from ortho-aminoaryl alkynes

  • Synthesis of indoles from ortho-alkylaryl isocyanides

  • Synthesis of indoles from ortho-acyl anilides

  • Synthesis of isatins from anilines

  • Synthesis of oxindoles from anilines

  • Synthesis of indoxyls from anthranilic acids

  • Azaindoles

  • Exercises