Bulk Gold-Catalyzed Reactions of Diazoalkanes with Amines and O-2 to Give Enamines

TitleBulk Gold-Catalyzed Reactions of Diazoalkanes with Amines and O-2 to Give Enamines
Publication TypeJournal Article
Year of Publication2010
AuthorsZhou YB, Angelici RJ, Woo LK
Journal TitleCatalysis Letters
Volume137
Pages8-15
Date Published06
ISBN Number1011-372X
Accession NumberISI:000277786100002
Keywordsaerobic oxidation, amines, CARBENE COMPLEXES, carbon-monoxide, catalysis, enamines, ethyl diazoacetate, Gold, h insertion reactions, n-h, non-nanogold catalysis, one-pot, oxidation, ruthenium porphyrin complexes, secondary-amines
Abstract

Bulk gold powder, consisting of approximately 5-50 mu m particles, catalyzes reactions of diazoalkanes E(H)C=N-2, where E is CO2Et or PhC(O), with amines (RRNH)-R-1-N-2 and O-2 to give enamine products ((RRN)-R-1-N-2) (E)C=CH(E) in 58-94% yield. The reactions are proposed to occur by initial formation of surface-bound (E)(H)C: carbene groups that are attacked by nucleophilic amines. The enamine products are very different than those obtained in reactions catalyzed by homogeneous transition metal complexes. These reactions of diazoalkanes, amines, and O-2 represent a new type of bulk gold-catalyzed reaction.

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