Rhodium-Catalyzed Alkylation of C−H Bonds in Aromatic Amides with Non-activated 1-Alkenes: The Possible Generation of Carbene Intermediates from Alkenes

Takuma Yamaguchi, Satoko Natsui, Kaname Shibata, Ken Yamazaki, Supriya Rej, Yusuke Ano, Naoto Chatani

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

The alkylation of C−H bonds (hydroarylation) in aromatic amides with non-activated 1-alkenes using a rhodium catalyst and assisted by an 8-aminoquinoline directing group is reported. The addition of a carboxylic acid is crucial for the success of this reaction. The results of deuterium-labeling experiments indicate that one of deuterium atoms in the alkene is missing, suggesting that the reaction does not proceed through the commonly accepted mechanism for C−H alkylation reactions. Instead the reaction is proposed to proceed through a carbene mechanism. The carbene mechanism is also supported by preliminary DFT calculations.

Original languageEnglish
Pages (from-to)6915-6919
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number28
DOIs
Publication statusPublished - May 17 2019
Externally publishedYes

Keywords

  • carbenes
  • C−H activation
  • non-activated alkenes
  • quinolinamide
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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