N-Alkylation of amines with alcohols catalyzed by a Cp*Ir complex

被引:266
作者
Fujita, K [1 ]
Li, ZZ
Ozeki, N
Yamaguchi, R
机构
[1] Kyoto Univ, Grad Sch Global Environm Studies, Dept Nat Resources, Kyoto 6068501, Japan
[2] Kyoto Univ, Grad Sch Human & Environm Studies, Kyoto 6068501, Japan
基金
日本学术振兴会;
关键词
iridium catalyst; N-alkylation; hydrogen transfer; amine; alcohol;
D O I
10.1016/S0040-4039(03)00371-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new effective catalytic system consisting of [Cp*IrCl2](2)/K2CO3 (Cp* = pentamethylcyclopentadienyl) for the N-alkylation of primary amines with alcohols has been developed. As an example, the reaction of aniline with benzyl alcohol in the presence of [Cp*IrCl2](2) (5.0 mol%Ir) and K2CO3 (5.0 mol%) in toluene at 110degreesC for 17 h gave benzylaniline in an isolated yield of 88%. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2687 / 2690
页数:4
相关论文
共 17 条
[1]   Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].
AbdelMagid, AF ;
Carson, KG ;
Harris, BD ;
Maryanoff, CA ;
Shah, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862
[2]   N-ALKYLATION OF AMINES VIA HOMOGENEOUS CATALYSIS - SYNTHESIS OF CYCLIC MONOAMINES AND DIAMINES [J].
BITSI, G ;
SCHLEIFFER, E ;
ANTONI, F ;
JENNER, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 373 (03) :343-352
[3]   Oxidative cyclization of amino alcohols catalyzed by a Cp*Ir complex. Synthesis of indoles, 1,2,3,4-tetrahydroquinolines, and 2,3,4,5-tetrahydro-1-benzazepine [J].
Fujita, K ;
Yamamoto, K ;
Yamaguchi, R .
ORGANIC LETTERS, 2002, 4 (16) :2691-2694
[4]   Oxidation of primary and secondary alcohols catalyzed by a pentamethylcyclopentadienyliridium complex [J].
Fujita, K ;
Furukawa, S ;
Yamaguchi, R .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 649 (02) :289-292
[5]   TRANSITION METAL-CATALYZED N-ALKYLATION OF AMINES BY ALCOHOLS [J].
GRIGG, R ;
MITCHELL, TRB ;
SUTTHIVAIYAKIT, S ;
TONGPENYAI, N .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (12) :611-612
[6]   RUTHENIUM CATALYZED N-METHYLATION OF AMINOARENES USING METHANOL [J].
HUH, KT ;
TSUJI, Y ;
KOBAYASHI, M ;
OKUDA, F ;
WATANABE, Y .
CHEMISTRY LETTERS, 1988, (03) :449-452
[7]   Asymmetric transfer hydrogenation of ketonic substrates catalyzed by (η5-C5Me5)MCl complexes (M = Rh and Ir) of (1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine [J].
Mashima, K ;
Abe, T ;
Tani, K .
CHEMISTRY LETTERS, 1998, (12) :1199-1200
[8]   RUTHENIUM CATALYZED SYNTHESIS OF SECONDARY OR TERTIARY-AMINES FROM AMINES AND ALCOHOLS [J].
MURAHASHI, S ;
KONDO, K ;
HAKATA, T .
TETRAHEDRON LETTERS, 1982, 23 (02) :229-232
[9]   New chiral rhodium and iridium complexes with chiral diamine ligands for asymmetric transfer hydrogenation of aromatic ketones [J].
Murata, K ;
Ikariya, T .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2186-2187
[10]   pH-dependent transfer hydrogenation, reductive amination, and dehalogenation of water-soluble carbonyl compounds and alkyl halides promoted by Cp*Ir complexes [J].
Ogo, S ;
Makihara, N ;
Kaneko, Y ;
Watanabe, Y .
ORGANOMETALLICS, 2001, 20 (23) :4903-4910