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Bulk Gold-Catalyzed Oxidations of Amines and Benzyl Alcohol Using Amine N-Oxides as Oxidants

TitleBulk Gold-Catalyzed Oxidations of Amines and Benzyl Alcohol Using Amine N-Oxides as Oxidants
Publication TypeJournal Article
Year of Publication2012
AuthorsKlobukowski ER, Angelici RJ, Woo LK
Journal TitleCatalysis Letters
Volume142
Pages161-167
Date Published02
Type of ArticleArticle
ISBN Number1011-372X
Accession NumberWOS:000299920100002
Keywordsaerobic oxidation, Alcohol, Amine, Amine N-oxide, catalysis, chemistry, Gold, Imine, imines, ISOCYANIDES, metal, nanoparticles, non-nanogold catalysis, oxidation, Oxidative-dehydrogenation, oxygen, secondary-amines, supported
Abstract

Bulk gold powder (similar to 50 mu m) catalyzes the oxidative dehydrogenation of amines to give imines using amine N-oxides (R3N-O) as the oxidant. The reaction of dibenzylamine (PhCH2-NH-CH2Ph) with N-methylmorpholine N-oxide (NMMO) in the presence of gold powder at 60 A degrees C produced N-benzylidenebenzylamine (PhCH=N-CH2Ph) in 96% yield within 24 h. Benzyl alcohol was oxidized by NMMO to benzaldehyde in > 60% yield in the presence of gold powder. Although O-2 was previously shown to oxidize amines in the presence of bulk gold, it is surprising that gold is also capable of catalyzing the oxidation of amines using amine oxides, which are chemically so different from O-2.
URL<Go to ISI>://WOS:000299920100002
DOI10.1007/s10562-011-0758-0
Alternate JournalCatal. Lett.