ORGN 204 |
Alkyl amines represent an important class of chemical transformations that have found extensive use in the construction of vast range of natural products, bioactive molecules, and industrial materials. Such broad utilities have made them important synthetic targets. A main traditional synthetic rout of alkyl amines is direct base-promoted N-alkylation although it includes a lot of problems, such as the use of toxic and corrosive alkylating reagents, the generation of a large quantity of wasteful salts as by-products, and over alkylation. These problems are undesirable in view of environmental concerns. To overcome these difficulties, we have developed Rh/C-catalyzed reductive and catalytic monoalkylation of primary amines using nitriles as alkylating reagents. During the course of further study, we have found the excellent catalytic activity of 10% Pd/C toward the quantitative formation of tertiary amines by the addition of NH4OAc. The present method for the synthesis of tertiary amines is applicable to a wide range of industrial systems.
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |