Ruthenium-catalyzed intramolecular oxidative amination of aminoalkenes enables rapid synthesis of cyclic imines

Teruyuki Kondo; Takumi Okada; Take-aki Mitsudo

doi:10.1021/ja017012k

Ruthenium-catalyzed intramolecular oxidative amination of aminoalkenes enables rapid synthesis of cyclic imines

J Am Chem Soc. 2002 Jan 16;124(2):186-7. doi: 10.1021/ja017012k.

Authors

Teruyuki Kondo¹, Takumi Okada, Take-aki Mitsudo

Affiliation

¹ Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.

PMID: 11782166
DOI: 10.1021/ja017012k

Abstract

[RuCl2(CO)3]2/dppp is shown to be a highly effective catalyst system for the first intramolecular oxidative amination of a variety of aminoalkenes when it is used concomitantly with K2CO3 and allyl acetate in N-methylpiperidine, to give the corresponding cyclic imines and indoles in excellent yields. For example, the reaction of 2,2-diphenyl-4-pentenyl-1-amine performed in the presence of 2 mol % of [RuCl2(CO)3]2, 4 mol % of dppp, K2CO3, and allyl acetate in N-methylpiperidine at 140 degrees C for 8 h gives 4,4-diphenyl-2-methyl-1-pyrroline in quantitative (>99%) yield.