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7917896 
Journal Article 
Cp*Ir-catalyzed N-alkylation of amines with alcohols. A versatile and atom economical method for the synthesis of amines 
Fujita, K; Enoki, Y; Yamaguchi, R 
2008 
1 
Tetrahedron
ISSN: 0040-4020 
64 
8 
1943-1954 
English 
WOS:000253620600046 
A versatile and highly atom economical catalytic system consisting of [Cp*IrCl2]2/NaHCO3 (Cp*=pentamethylcyclopentadienyl) for the N-alkylation of amines with primary and secondary alcohols as alkylating reagents has been developed. For example, the reaction of equimolar amounts of aniline and benzyl alcohol in the presence of [Cp*IrCl2]2 (1.0 mol % Ir) and NaHCO3 (1.0 mol %) in toluene at 110 °C gives N-benzylaniline in 94% yield. The present catalytic system is applicable to the N-alkylation of both primary and secondary amines, and only harmless water is produced as co-product. A wide variety of secondary and tertiary amines can be synthesized with high atom economy under mild and less-toxic conditions. One-pot sequential N-alkylation leading to tertiary amines bearing three different substituents is also described. © 2007 Elsevier Ltd. All rights reserved. 
iridium catalyst; hydrogen transfer; N-alkylation; amine; alcohol