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PdII -Catalyzed Regio- and Enantioselective Oxidative C-H/C-H Cross-Coupling Reaction between Ferrocenes and Azoles.

Zhong-Jian CaiChen-Xu LiuQing GuChao ZhengShu-Li You
Published in: Angewandte Chemie (International ed. in English) (2019)
Asymmetric C-H bond functionalization reaction is one of the most efficient and straightforward methods for the synthesis of optically active molecules. Herein we disclose an asymmetric C-H/C-H cross-coupling reaction of ferrocenes with azoles such as oxazoles and thiazoles. Palladium(II)/monoprotected amino acid (MPAA) catalytic system which exhibits excellent reactivity and regioselectivity for oxazoles and thiazoles. This method offers a powerful strategy for constructing planar chiral ferrocenes. Mechanistic studies suggest that the C-H bond cleavage of azoles is likely proceeding through a SE Ar process and may not be a turnover limiting step.
Keyphrases
  • amino acid
  • electron transfer
  • room temperature
  • solid state
  • ionic liquid
  • dna binding
  • mass spectrometry
  • transition metal