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 featured 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. Over the past decades the “dark-side” of indole reactivity: electrophilicity, has been elegantly investigated, providing chemically competent towards the realization of specific interatomic connections that would be difficult to obtain by means of conventional indole reactivity. The present MiniReview article wishes to summarize the major findings that brought the research area from the pioneering findings in the 60s to the state of the art.Indole is by far one of the most popular heterocyclic scaffolds in nature.
Org. Biomol. Chem., 2013, Accepted Manuscript