Benzylic C(sp3)-H Perfluoroalkylation of Six-Membered Heteroaromatic Compounds

Yoichiro Kuninobu, Masahiro Nagase, Motomu Kanai

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34 Citations (Scopus)

Abstract

Successful benzylic C(sp3)-H trifluoromethylation, pentafluoroethylation, and heptafluoropropylation of six-membered heteroaromatic compounds were achieved as the first examples of a practical benzylic C(sp3)-H perfluoroalkylation. In these reactions, BF2CnF2n+1 (n=1-3) functioned as both a Lewis acid to activate the benzylic position and a CnF2n+1 (n=1-3) source. The perfluoroalkylation proceeded at both terminal and internal positions of the alkyl chains. Perfluoroalkylated products were obtained in moderate to excellent yields, even on gram scale, and in a sequential procedure without isolation of the intermediates. By using this method, trifluoromethylation of a bioactive compound, as well as introduction of a CF3 group into a bioactive molecular skeleton, proceeded regioselectively.

Original languageEnglish
Pages (from-to)10263-10266
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number35
DOIs
Publication statusPublished - Aug 1 2015
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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