4-Position-Selective C-H Perfluoroalkylation and Perfluoroarylation of Six-Membered Heteroaromatic Compounds

Masahiro Nagase, Yoichiro Kuninobu, Motomu Kanai

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

The first 4-position-selective C-H perfluoroalkylation and perfluoroarylation of six-membered heteroaromatic compounds were achieved using nucleophilic perfluoroalkylation and perfluoroarylation reagents. The regioselectivity was controlled by electrophilically activating the heteroaromatic rings, while sterically hindering the 2-position, with a sterically bulky borane Lewis acid. The reaction proceeded in good yield, even in gram scale, and by a sequential reaction without isolating the intermediates. This reaction could be applied to late-stage trifluoromethylation of a bioactive compound.

Original languageEnglish
Pages (from-to)6103-6106
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number19
DOIs
Publication statusPublished - May 18 2016
Externally publishedYes

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Boranes
Lewis Acids
Regioselectivity
Acids

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

4-Position-Selective C-H Perfluoroalkylation and Perfluoroarylation of Six-Membered Heteroaromatic Compounds. / Nagase, Masahiro; Kuninobu, Yoichiro; Kanai, Motomu.

In: Journal of the American Chemical Society, Vol. 138, No. 19, 18.05.2016, p. 6103-6106.

Research output: Contribution to journalArticle

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