Affiliation:
1. Department of Biological Science and Technology, Faculty of Advanced Engineering Tokyo University of Science 6-3-1 Niijuku, Katsushika-ku Tokyo 125-8585 Japan
Abstract
AbstractSingle 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 o‐hydrosilyl‐substituted benzotrifluorides through the hydride abstraction with trityl cations. Single C−F thiolation and azidation of o‐(hydrosilyl)benzotrifluorides were achieved using trityl sulfides and trityl azide catalyzed by Yb(OTf)3. Treatment of o‐(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 LiAlH4‐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.
Subject
Materials Chemistry,General Chemical Engineering,Biochemistry,General Chemistry
Cited by
5 articles.
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