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Palladium-Catalyzed Dearomative syn-1,4-Carboamination with Grignard Reagents

Articolo
Data di Pubblicazione:
2019
Abstract:
A protocol for palladium-catalyzed dearomative functionalization of simple, nonactivated arenes with Grignard reagents has been established. This one-pot method features a visible-light-mediated [4+2] cycloaddition between an arene and an arenophile, and subsequent palladium-catalyzed allylic substitution of the resulting cycloadduct with a Grignard reagent. A variety of arenes and Grignard reagents can participate in this process, forming carboaminated products with exclusive syn-1,4-selectivity. Moreover, the dearomatized products are amenable to further elaborations, providing functionalized alicyclic motifs and pharmacophores. For example, naphthalene was converted into sertraline, one of the most prescribed antidepressants, in only four operations. Finally, this process could also be conducted in an enantioselective fashion, as demonstrated with the desymmetrization of naphthalene.
Tipologia CRIS:
1.1 Articolo in rivista
Keywords:
arenes; aromaticity; cycloadditions; palladium; photochemistry; Antidepressive Agents; Catalysis; Models, Molecular; Molecular Structure; Naphthalenes; Palladium; Sertraline
Elenco autori:
Tang, C.; Okumura, M.; Zhu, Y.; Hooper, A. R.; Zhou, Y.; Lee, Y. -H.; Sarlah, D.
Autori di Ateneo:
SARLAH DAVID
Link alla scheda completa:
https://iris.unipv.it/handle/11571/1370019
Pubblicato in:
ANGEWANDTE CHEMIE. INTERNATIONAL EDITION
Journal
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