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Article Dans Une Revue Chemical Communications Année : 2021

Reactivity of 3-nitroindoles with electron-rich species

Résumé

The indol(in)e building block is one of the "privileged-structures" for the pharmaceutical industry since this fragment plays a central role in drug discovery. While the electron-rich character of the indole motif has been investigated for decades, exploiting the electrophilic reactivity of 3-nitroindole derivatives has recently been put at the heart of a wide range of new, albeit challenging, chemical reactions. In particular, dearomatization processes have considerably enriched the scope of C2=C3 functionalizations of these scaffolds. This feature article showcases this remarkable electrophilic reactivity of 3-nitroindoles with electron-rich species and highlights their value to generate diversely substituted indol(in)es. This compilation underlines how these heteroaromatic templates have gradually become model substrates for electron-poor aromatic compounds in dearomatization strategies.

Domaines

Chimie
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Dates et versions

hal-03353838 , version 1 (09-12-2020)
hal-03353838 , version 2 (28-09-2021)

Identifiants

Citer

Batoul Rkein, Antoine Bigot, Léo Birbaum, Maxime Manneveau, Michaël de Paolis, et al.. Reactivity of 3-nitroindoles with electron-rich species. Chemical Communications, 2021, 57 (1), pp.27-44. ⟨10.1039/D0CC06658C⟩. ⟨hal-03353838v2⟩
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