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Benzylic C(sp 3 )H Perfluoroalkylation of Six‐Membered Heteroaromatic Compounds
Author(s) -
Kuninobu Yoichiro,
Nagase Masahiro,
Kanai Motomu
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201505335
Subject(s) - trifluoromethylation , chemistry , alkyl , stereochemistry , lewis acids and bases , medicinal chemistry , organic chemistry , catalysis , trifluoromethyl
Successful benzylic C(sp 3 )H trifluoromethylation, pentafluoroethylation, and heptafluoropropylation of six‐membered heteroaromatic compounds were achieved as the first examples of a practical benzylic C(sp 3 )H perfluoroalkylation. In these reactions, BF 2 C n F 2 n +1 ( n =1–3) functioned as both a Lewis acid to activate the benzylic position and a C n F 2 n +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 CF 3 group into a bioactive molecular skeleton, proceeded regioselectively.