Tetrahedron Letters

Zinc-promoted, iridium catalyzed reductive alkylation of primary amines with aliphatic ketones in aqueous medium

RA da Silva, LW Bieber

Index: da Silva, Renato A.; Bieber, Lothar W. Tetrahedron Letters, 2010 , vol. 51, # 4 p. 689 - 691

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Citation Number: 6

Abstract

The reductive alkylation of primary aromatic and aliphatic amines with aliphatic ketones has been achieved in aqueous acidic medium using commercially available, non-activated zinc dust catalyzed by a very small quantity of iridium bromide. Anilines react well in aqueous formic acid, whereas monoalkylamines require 1, 4-dioxane as a co-solvent and sulfuric acid as the proton source. A plausible mechanism via low-valent iridium hydride species ...