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Issue 32, 2013
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Electrophilicity: the “dark-side” of indole chemistry

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Abstract

Indole is by far one of the most popular heterocyclic scaffolds in nature. The intriguing and challenging molecular architectures of polycyclic, naturally occurring indolyl compounds constitute a continuous stimulus for development in organic synthesis. The field had a formidable boom across the new millennium when catalysis started revolutionizing the chemistry of indole, providing always more convincing and sustainable solutions to the selective “decoration” of this pharmacophore. A common guideline of these approaches relies on the intrinsic overexpression of electron density of the indole core. Despite less diffusion, the “dark-side” of indole reactivity, electrophilicity, has been also elegantly documented with direct applications towards the realization of specific interatomic connections that would be difficult to obtain by means of conventional indole reactivity. The present Perspective article summarizes the major findings that brought the research area from the pioneering findings of the 60s to the state of the art.

Graphical abstract: Electrophilicity: the “dark-side” of indole chemistry

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Article information


Submitted
12 Apr 2013
Accepted
17 Jun 2013
First published
18 Jun 2013

Org. Biomol. Chem., 2013,11, 5206-5212
Article type
Perspective

Electrophilicity: the “dark-side” of indole chemistry

M. Bandini, Org. Biomol. Chem., 2013, 11, 5206
DOI: 10.1039/C3OB40735G

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