Journal
TETRAHEDRON
Volume 65, Issue 18, Pages 3624-3628Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.03.002
Keywords
Iridium catalyst; N-Alkylation; Carbamate; Alcohol
Categories
Funding
- KAKENHI [19550106]
- Grants-in-Aid for Scientific Research [19550106] Funding Source: KAKEN
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New atom-economical catalytic systems consisting of [Cp*IrCl2](2)/NaOAc (Cp*=pentamethylcyclopentadienyl) for the N-alkylation of carbamates and amides using alcohols as alkylating agents under solvent-free conditions have been developed. For example, the reaction of n-butyl carbamate with benzyl alcohol in the presence of [Cp*IrCl2](2) (5.0 mol % Ir) and NaOAc (5.0 mol %) at 130 degrees C under the absence of solvent gives n-butyl N-benzylcarbamate in the yield of 94%. The present catalytic system is applicable to not only carbamates but also amides, and only harmless water is produced as co-product. (C) 2009 Elsevier Ltd. All rights reserved.
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