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Effective Oxidation of Secondary Amines to Nitrones with Alkyl Hydroperoxides Catalysed by (Trialkanolaminato)titanium(IV) Complexes
Author(s) -
Forcato Massimiliano,
Mba Miriam,
Nugent William A.,
Licini Giulia
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900867
Subject(s) - chemistry , catalysis , anhydrous , alkoxide , alkyl , selectivity , titanium , molecular sieve , solvent , organic chemistry , homogeneous catalysis , ligand (biochemistry) , biochemistry , receptor
The effective catalytic oxidation of secondary amines to nitrones with alkyl hydroperoxides as the primary oxidants is described. The titanium alkoxide catalysts are protected from the water co‐product by the combined use of a tightly binding trialkanolamine ligand and molecular sieves. Nitrones can be obtained in high yields (up to 98 %) under homogeneous, anhydrous conditions and even in the absence of solvent. The reactions are fast (2–7 h) and good selectivity and complete conversion can be achieved with as little as 1 % catalyst.