Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 9, Issue -, Pages 2451-2456Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.283
Keywords
C-F bond activation; highly concentrated conditions; nucleophilic substitution; hydrogen bond; organofluorine; triol
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Funding
- Canada Research Chair Program
- Natural Sciences and Engineering Research Council of Canada
- Canada Foundation for Innovation
- FRQNT Centre in Green Chemistry and Catalysis (CGCC)
- FQRNT Network for Research on Protein Function, Structure, and Engineering (PROTEO)
- Universite Laval
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Activation of the C-F bond of benzylic fluorides was achieved using 1,1,1-tris(hydroxymethyl)propane (2) as a hydrogen bond-donating agent. Investigations demonstrated that hydrogen bond-donating solvents are promoting the activation and hydrogen bond-accepting ones are hindering it. However, the reaction is best run under highly concentrated conditions, where solvents cannot interfere with the interaction between the organofluorine compound and the triol. Various benzylic fluorides react with secondary amines or anilines to form benzylic amines in good yields.
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