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Electrophilic Substitution Reactions of Indoles

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Heterocyclic Scaffolds II:

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 26))

Abstract

The topic of this chapter is electrophilic substitution of indole and its derivatives. The indole ring is highly reactive at its 3-position toward protonation, halogenation, alkylation and acylation. Electrophilic substitution can be combined with inter- or intramolecular addition at C-2. Intramolecular alkylation by iminium ions (Pictet-Spengler reaction) is particularly useful. Enantioselectivity can be achieved in many conjugate addition reactions. These reactions have been applied to synthesis of both natural products and drugs.

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  1. Department of Chemistry, University of Virginia, Charlottesville, VA, 22904, USA

    Richard J. Sundberg

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  1. Richard J. Sundberg
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Correspondence to Richard J. Sundberg .

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  1. Dept. Chemistry, Dartmouth College, Burke Laboratory 6128, Hanover, 03755, New Hampshire, USA

    Gordon W. Gribble

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Sundberg, R.J. (2010). Electrophilic Substitution Reactions of Indoles. In: Gribble, G. (eds) Heterocyclic Scaffolds II:. Topics in Heterocyclic Chemistry, vol 26. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2010_52

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