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C−F Transformations of Benzotrifluorides by the Activation of <i>Ortho</i>‐Hydrosilyl Group
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- Suguru Yoshida
- Department of Biological Science and Technology, Faculty of Advanced Engineering Tokyo University of Science 6-3-1 Niijuku, Katsushika-ku Tokyo 125-8585 Japan
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Description
<jats:title>Abstract</jats:title><jats:p>Single C−F transformations of aromatic trifluoromethyl compounds are challenging issues due to the strong C−F bond. We have recently developed selective methods for single C−F transformations such as allylation of <jats:italic>o</jats:italic>‐hydrosilyl‐substituted benzotrifluorides through the hydride abstraction with trityl cations. Single C−F thiolation and azidation of <jats:italic>o</jats:italic>‐(hydrosilyl)benzotrifluorides were achieved using trityl sulfides and trityl azide catalyzed by Yb(OTf)<jats:sub>3</jats:sub>. Treatment of <jats:italic>o</jats:italic>‐(hydrosilyl)benzotrifluorides with trityl chloride resulted in single C−F chlorination. The resulting fluorosilyl group served in further transformations including protonation, halogenation, and Hiyama cross‐coupling with C−Si cleavage. We also synthesized benzyl fluorides by LiAlH<jats:sub>4</jats:sub>‐reduction of the resulting fluorosilanes and further C−F transformations. These methods enabled us to prepare a broad range of organofluorines from simple benzotrifluorides through C−F and C−Si transformations.</jats:p>
Journal
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- The Chemical Record
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The Chemical Record 23 (9), e202200308-, 2023-02-10
Wiley
