Selective one-pot synthesis of symmetrically and unsymmetrically substituted amines via rhodium catalysed multiple alkylations of ammonia or primary amines under hydroformylation conditions

被引:60
作者
Rische, T [1 ]
Kitsos-Rzychon, B [1 ]
Eilbracht, P [1 ]
机构
[1] Univ Dortmund, FB 3, D-44221 Dortmund, Germany
关键词
D O I
10.1016/S0040-4020(98)83008-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Symmetrically and unsymmetrically substituted secondary and tertiary amines are selectively prepared in high yields by a one-pot multiple alkylation procedure from ammonia or primary amines with styrenes and/or cyclic olefins, carbon monoxide and hydrogen in the presence of [Rh(cod)Cl](2) as catalyst. Similarly unsymmetrically substituted tertiary amines are obtained under hydroformylation conditions from primary amines by a one-pot reductive bisalkylation procedure using preformed aldehydes or ketones in one step and the hydroformylation products in the second step of a combined amine condensation-reduction-hydroaminomethylation reaction sequence. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2723 / 2742
页数:20
相关论文
共 40 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]   HYDROFORMYLATION OF UNSATURATED COMPOUNDS WITH A COBALT CARBONYL CATALYST [J].
ADKINS, H ;
KRSEK, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (09) :3051-3055
[3]   CARBON-MONOXIDE AS A BUILDING-BLOCK IN ORGANIC-SYNTHESIS .4. DIRECT PREPARATION OF AMINES FROM ALKENES BY AMINOMETHYLATION CATALYZED BY DINUCLEAR RHODIUM COMPLEXES [J].
BAIG, T ;
MOLINIER, J ;
KALCK, P .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 455 (1-2) :219-224
[4]   ONE-POT SYNTHESIS OF AMINES BY AMINOMETHYLATION OF ALKENES CATALYZED BY DINUCLEAR RHODIUM COMPLEXES UNDER MILD CONDITIONS [J].
BAIG, T ;
KALCK, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (18) :1373-1374
[5]   PROGRESS IN HYDROFORMYLATION AND CARBONYLATION [J].
BELLER, M ;
CORNILS, B ;
FROHNING, CD ;
KOHLPAINTNER, CW .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 104 (01) :17-85
[6]   UNEXPECTED NON-INFLUENCE OF THE PHOSPHINE RHODIUM RATIO ON THE ACTIVITY AND SELECTIVITY OF RHODIUM PHOSPHINE HYDROFORMYLATION CATALYSTS [J].
BERGOUNHOU, C ;
NEIBECKER, D ;
REAU, R .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (20) :1370-1372
[7]  
Biale G., 1970, U.S. Patent, Patent No. 3513200
[8]  
BROWN HC, 1981, SYNTHESIS-STUTTGART, P996
[9]   IRON PENTACARBONYL-CATALYZED AMINOMETHYLATION OF ALKENES - SOME INTRIGUING OBSERVATIONS [J].
BRUNET, JJ ;
NEIBECKER, D ;
AGBOSSOU, F ;
SRIVASTAVA, RS .
JOURNAL OF MOLECULAR CATALYSIS, 1994, 87 (2-3) :223-230
[10]  
DALTON JC, 1973, TETRAHEDRON LETT, V34, P3145