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

Conghui Tang, Mikiko Okumura, Yunbo Zhu, Annie R. Hooper, Yu Zhou, Yu Hsuan Lee, David Sarlah

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)10245-10249
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number30
DOIs
StatePublished - Jul 22 2019

Keywords

  • arenes
  • aromaticity
  • cycloadditions
  • palladium
  • photochemistry

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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