The titanocene-catalyzed reduction of acetamides to tertiary amines by PhMeSiH2
- 1 August 2004
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 82 (8) , 1244-1248
- https://doi.org/10.1139/v04-063
Abstract
A variety of acetamide derivatives are reduced in excellent yields to tertiary amines by PhMeSiH2 in the presence of Cp2TiX2 (X = F or Me) catalysts. The reactions are very clean at 80 °C. At room temperature a secondary reaction, hydrogenolysis of the C(O)—N bond, intervenes and reduces the chemoselectivity. Nevertheless, this chemistry provides a simple methodology for the amide/alkylamine transformation using inexpensive, commercially available reagents.Key words: amides, reduction, secondary amides, methylphenylsilane, titanocene, catalysis.Keywords
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