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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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Publication details

The article was received on 12 Apr 2013, accepted on 17 Jun 2013 and first published on 18 Jun 2013


Article type: Perspective
DOI: 10.1039/C3OB40735G
Citation: Org. Biomol. Chem., 2013,11, 5206-5212
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    Electrophilicity: the “dark-side” of indole chemistry

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

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