Direct Carboxylation of Electron-Rich Heteroarenes Promoted by LiO-tBu with CsF and [18]Crown-6

Masanori Shigeno, Kazuya Hanasaka, Keita Sasaki, Kanako Nozawa-Kumada, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

We herein demonstrate that the combination of LiO-tBu, CsF, and [18]crown-6 efficiently promotes the direct C−H carboxylation of electron-rich heteroarenes (benzothiophene, thiophene, benzofuran, and furan derivatives). A variety of functional groups, including methyl, methoxy, halo, cyano, amide, and keto moieties, are compatible with this system. The reaction proceeds via the formation of a tert-butyl carbonate species.

Original languageEnglish
Pages (from-to)3235-3239
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number13
DOIs
Publication statusPublished - 2019 Mar 1

Keywords

  • Brønsted base
  • C−H functionalization
  • carbon dioxide
  • carboxylation
  • heterocycles

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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