Sodium periodate/TEMPO as a selective and efficient system for amine oxidationElectronic supplementary information (ESI) available: General procedures for the synthesis of the secondary amines 7-11via imines 4a, 4m, 4n, 4o, and 4t, and NMR spectra of compounds. See DOI: 10.1039/c8ra01365a

A new metal-free protocol for promoting oxidation of amines in aqueous-organic medium was developed. NaIO 4 and TEMPO as the catalyst emerged as the most efficient and selective system for oxidation of differently substituted benzyl amines to the corresponding benzaldehydes without overoxidation. Un...

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Main Authors: Galletti, P, Martelli, G, Prandini, G, Colucci, C, Giacomini, D
Format: Article
Language:English
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Summary:A new metal-free protocol for promoting oxidation of amines in aqueous-organic medium was developed. NaIO 4 and TEMPO as the catalyst emerged as the most efficient and selective system for oxidation of differently substituted benzyl amines to the corresponding benzaldehydes without overoxidation. Unsymmetrical secondary amines underwent selective oxidation only at the benzylic position thus realising an oxidative deprotection of a benzylic group with an easy amine recovery. NaIO 4 /TEMPO efficiently allowed a metal-free oxidation of benzylamines to benzaldehydes with complete selectivity for N -benzyl residues in secondary amines.
ISSN:2046-2069
DOI:10.1039/c8ra01365a