Convenient and clean synthesis of imines from primary benzylamines
Authors:
- 16 August 2010
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 8 (20) , 4716-4719
Abstract
The current syntheses of imines from benzylamines are often performed in organic solvents or under harsh reaction conditions. Clean oxidation of primary benzylamines to imines has been successfully achieved using H2O2 in water at room temperature catalyzed by V2O5. Among the 10 imine products, 5 of them precipitated from the reaction and led pure products after simple filtration. No organic solvents are needed in the whole process. The yields are good to quantitative. This represents an efficient and green procedure of the synthesis of imines. A similar green oxidation of benzylamines to aromatic aldehydes is also reported. A benzylic anion-involved mechanism is proposed based on the experiments.Keywords
This publication has 29 references indexed in Scilit:
- Highly Efficient Oxidation of Amines to Imines by Singlet Oxygen and Its Application in Ugi-Type ReactionsOrganic Letters, 2009
- Catalytic dehydrogenation of aliphatic amines to nitriles, imines, or vinylamines and dealkylation of tertiary aliphatic amines over halide cluster catalysts of group 5 and 6 transition metalsJournal of Catalysis, 2005
- o-Iodoxybenzoic Acid (IBX) as a Viable Reagent in the Manipulation of Nitrogen- and Sulfur-Containing Substrates: Scope, Generality, and Mechanism of IBX-Mediated Amine Oxidations and Dithiane DeprotectionsJournal of the American Chemical Society, 2004
- Copper-Catalyzed Oxidation of Amines with Molecular OxygenBulletin of the Chemical Society of Japan, 2003
- Scope, Kinetics, and Mechanistic Aspects of Aerobic Oxidations Catalyzed by Ruthenium Supported on AluminaChemistry – A European Journal, 2003
- New Reactions of IBX: Oxidation of Nitrogen‐ and Sulfur‐Containing Substrates To Afford Useful Synthetic IntermediatesAngewandte Chemie International Edition, 2003
- Efficient Heterogeneous Aerobic Oxidation of Amines by a Supported Ruthenium CatalystAngewandte Chemie International Edition, 2003
- Catalysis of a hydroxyapatite-bound Ru complex: efficient heterogeneous oxidation of primary amines to nitriles in the presence of molecular oxygenChemical Communications, 2001
- Synthetic Aspects of Metal‐Catalyzed Oxidations of Amines and Related ReactionsAngewandte Chemie International Edition, 1995
- Selective aerobic oxidative dehydrogenation of alcohols and amines catalyzed by a supported molybdenum-vanadium heteropolyanion salt Na5PMo2V2O40The Journal of Organic Chemistry, 1991