3-Position-Selective C-H Trifluoromethylation of Pyridine Rings Based on Nucleophilic Activation

Ryuhei Muta, Takeru Torigoe, Yoichiro Kuninobu

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The first example of the 3-position-selective C(sp2)-H trifluoromethylation of pyridine rings was established. 3-Position-selective trifluoromethylation was achieved by the nucleophilic activation of pyridine and quinoline derivatives through hydrosilylation and successive electrophilic trifluoromethylation of the enamine intermediate. This reaction was applicable to perfluoroalkylation at the 3 position of the pyridine rings and late-stage trifluoromethylation of a bioactive molecule. Mechanistic studies indicated that the reaction proceeds via the formation of N-silyl enamine and trifluoromethylated enamine intermediates.

Original languageEnglish
Pages (from-to)8218-8222
Number of pages5
JournalOrganic letters
Volume24
Issue number44
DOIs
Publication statusPublished - Nov 11 2022

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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