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A B(C6F5)3-catalyzed reductive denitrogenation of aromatic nitriles is reported, achieving the metal-free transformation of a cyano into a methyl group in a single synthetic operation. Tris(phenylsilyl)amine is liberated as the… Click to show full abstract
A B(C6F5)3-catalyzed reductive denitrogenation of aromatic nitriles is reported, achieving the metal-free transformation of a cyano into a methyl group in a single synthetic operation. Tris(phenylsilyl)amine is liberated as the nitrogen-containing byproduct. On the basis of control experiments as well as a nuclear magnetic resonance spectroscopic analysis, an SN1-type mechanism involving a trisilylammonium ion as a key intermediate is proposed.
Keywords:
denitrogenation benzonitrile;
reductive denitrogenation;
c6f5 catalyzed;
benzonitrile derivatives;
catalyzed reductive
Journal Title: Organic letters
Year Published: 2022
Link to full text (if available)
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Journal Title: Organic letters
Year Published: 2022
Link to full text (if available)
Share on Social Media: Sign Up to like & get
recommendations!