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

来源：

TETRAHEDRON | 1998年 / 54卷 / 12期

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

页码：2723 / 2742

页数：20

共 40 条

[31]

Larson A T., 1950, U. S. Patent, Patent No. 2497310

[32]

MACENTIRE EE, 1987, Patent No. 240193

[33]

Marson C. M., 1995, Comprehensive Organic Functional Group Transformations, V2, P297

[34]

Mitsunobu O., 1991, Comprehensive Organic Synthesis, V6, P65

[35] CARBONYLATIONS WITH CO/H2O AND CO/H2 CATALYZED BY CO2(CO)8-1,2-BIS(DIPHENYLPHOSPHINO)ETHANE COMPLEXES [J].

MURATA, K ;

MATSUDA, A ;

MASUDA, T .

JOURNAL OF MOLECULAR CATALYSIS, 1984, 23 (01) :121-132

[36]

Olin JF, 1947, United States Patent, Patent No. [2,422,631, 2422631]

[37]

REPPE W, 1953, LIEBIGS ANN CHEM, V582, P133

[38] UBER DIE DURCH METALLCARBONYLVERBINDUNGEN KATALYSIERTE UMSETZUNG VON OLEFINEN MIT KOHLENOXYD UND AMMONIAK BZW AMINEN IN GEGENWART VON WASSERSTOFF [J].

STRIEGLE.A ;

WEBER, J .

JOURNAL FUR PRAKTISCHE CHEMIE, 1965, 29 (3-6) :281-&

[39] SYNTHESIS OF NEW FORMYL AND AMINOMETHYL STEROIDS VIA HOMOGENEOUS CATALYSIS [J].

TOROS, S ;

GEMESPECSI, I ;

HEIL, B ;

MAHO, S ;

TUBA, Z .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (11) :858-859

[40]

WIELAND G, 1985, LIEBIGS ANN CHEM, P2178

← 1 2 3 4 →