Benzylic C(sp<sup>3</sup>)H Perfluoroalkylation of Six‐Membered Heteroaromatic Compounds
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<jats:title>Abstract</jats:title><jats:p>Successful benzylic C(sp<jats:sup>3</jats:sup>)H trifluoromethylation, pentafluoroethylation, and heptafluoropropylation of six‐membered heteroaromatic compounds were achieved as the first examples of a practical benzylic C(sp<jats:sup>3</jats:sup>)H perfluoroalkylation. In these reactions, BF<jats:sub>2</jats:sub>C<jats:sub><jats:italic>n</jats:italic></jats:sub>F<jats:sub>2<jats:italic>n</jats:italic>+1</jats:sub> (<jats:italic>n</jats:italic>=1–3) functioned as both a Lewis acid to activate the benzylic position and a C<jats:sub><jats:italic>n</jats:italic></jats:sub>F<jats:sub>2<jats:italic>n</jats:italic>+1</jats:sub> (<jats:italic>n</jats:italic>=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<jats:sub>3</jats:sub> group into a bioactive molecular skeleton, proceeded regioselectively.</jats:p>
収録刊行物
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- Angewandte Chemie International Edition
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Angewandte Chemie International Edition 54 (35), 10263-10266, 2015-07-29
Wiley
