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Salicylic Acid‐Catalyzed One‐Pot Hydrodeamination of Aromatic Amines by tert ‐Butyl Nitrite in Tetrahydrofuran
Author(s) -
FelipeBlanco Diego,
Alonso Francisco,
GonzalezGomez Jose C.
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700475
Subject(s) - chemistry , tetrahydrofuran , salicylic acid , catalysis , nitrite , aryl , radical , hydrogen peroxide , organic chemistry , benzene , medicinal chemistry , solvent , biochemistry , nitrate , alkyl
A significant acceleration in the hydrodeamination of in situ formed diazonium salts (from aromatic amines) has been observed in the presence of 10‐mol% salicylic acid, using tetrahydrofuran as the hydrogen donor. The reaction proceeds efficiently at 20 °C for a wide range of substituted anilines, even at 10‐mmol scale, without any other additive. The same protocol has been adapted to the selective deuterodeamination of some aromatic amines. Control experiments clearly show that aryl radicals are involved in the reaction mechanism.