4.8 Article

One-pot synthesis of nitrones from primary amines and aldehydes catalyzed by methyltrioxorhenium

Journal

CHEMSUSCHEM
Volume 1, Issue 4, Pages 327-332

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.200700156

Keywords

domino reactions; nitrogen oxides; oxidation; rhenium; sustainable chemistry

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One-pot condensation/oxidation of primary amines and aldehydes using urea-hydrogen peroxide (UHP) as the stoichiometric oxidant in the presence of methyltrioxorhenium (MTO) as catalyst affords nitrones in a simple and regioselective manner. UHP is a practical and safe source of H2O2, and its use here instead of aqueous H2O2 solutions also simplifies greatly the workup procedure cis extractions with organic solvents con be avoided. Typically, at the end of the reaction the solid urea is simply filtered off From a sustainability point of view, this one-pot synthesis is simple to perform, takes place under mild conditions, has a high atom economy, and releases water as the only by-product.

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