Cp∗Ir-catalyzed N-alkylation of amines with alcohols. A versatile and atom economical method for the synthesis of amines
2007; Elsevier BV; Volume: 64; Issue: 8 Linguagem: Inglês
10.1016/j.tet.2007.11.083
ISSN1464-5416
AutoresKen‐ichi Fujita, Youichiro Enoki, Ryohei Yamaguchi,
Tópico(s)Chemical Synthesis and Reactions
ResumoA 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.
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