A new class of catalysts with superior activity and selectivity for amidocarbonylation reactions

被引：25

作者：

Beller, M ^{[1
]}

Eckert, MK ^{[1
]}

Vollmuller, F ^{[1
]}

机构：

[1] Tech Univ Munich, Dept Inorgan Chem, D-85747 Garching, Germany

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 1998年 / 135卷 / 01期

关键词：

amidocarbonylation; palladium; catalysis; N-acyl amino acids; multi-component reaction;

D O I：

10.1016/S1381-1169(97)00286-0

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

For the first time, a detailed investigation of the newly developed palladium (Pd)-catalyzed amidocarbonylation for the synthesis of various N-acyl amino acids is described. A screening of important parameters led to a highly efficient process with the active catalyst system PdBr2/LiBr/H2SO4. Based on our study of the influence of solvent, temperature, pressure, co-catalysts and substrates, we draw up a profile of the Pd-catalyzed amidocarbonylation and discuss the mechanism in detail. The successful employment of acetals and various aldehydes as starting materials demonstrates the synthetic potential of this atomeconomic process. (C) 1998 Elsevier Science B.V. All rights reserved.

引用

页码：23 / 33

页数：11

共 28 条

[1] INTIMATE MECHANISM OF OXIDATIVE ADDITION TO ZEROVALENT PALLADIUM COMPLEXES IN THE PRESENCE OF HALIDE-IONS AND ITS RELEVANCE TO THE MECHANISM OF PALLADIUM-CATALYZED NUCLEOPHILIC SUBSTITUTIONS
AMATORE, C
JUTAND, A
SUAREZ, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) : 9531 - 9541
[2] ROLE AND EFFECTS OF HALIDE-IONS ON THE RATES AND MECHANISMS OF OXIDATIVE ADDITION OF IODOBENZENE TO LOW-LIGATED ZEROVALENT PALLADIUM COMPLEXES PD0(PPH3)2
AMATORE, C
AZZABI, M
JUTAND, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) : 8375 - 8384
[3] STABILIZATION OF BIS(TRIPHENYLPHOSPHINE)PALLADIUM(0) BY CHLORIDE-IONS - ELECTROCHEMICAL GENERATION OF HIGHLY REACTIVE ZEROVALENT PALLADIUM COMPLEXES
AMATORE, C
AZZABI, M
JUTAND, A
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 363 (03) : C41 - C45
[4] THE CROSS-COUPLING REACTIONS OF ORGANIC HALIDES WITH ORGANIC DERIVATIVES OF TIN, MERCURY AND COPPER CATALYZED BY PALLADIUM
BELETSKAYA, IP
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 250 (01) : 551 - 564
[5] Beller M, 1998, EUR J INORG CHEM, P29
[6] Palladium-catalyzed amidocarbonylation - A new, efficient synthesis of N-acyl amino acids
Beller, M
Eckert, M
Vollmuller, F
Bogdanovic, S
Geissler, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14): : 1494 - 1496
[7] Synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine derivatives: The central amino acid of vancomycin and related agents
Boger, DL
Borzilleri, RM
Nukui, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) : 3561 - 3565
[8] Synthesis and use of enantiomerically pure tert-leucine
Bommarius, AS
Schwarm, M
Stingl, K
Kottenhahn, M
Huthmacher, K
Drauz, K
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (12) : 2851 - 2888
[9] Nucleophilic aromatic substitution - A possible key step in total syntheses of vancomycin
Burgess, K
Lim, D
Martinez, CI
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (10): : 1077 - 1078
[10] LEVULINIC ACID SYNTHESIS VIA REGIOSPECIFIC CARBONYLATION OF METHYL VINYL KETONE OR OF ITS REACTION-PRODUCTS WITH HYDROCHLORIC-ACID OR AN ALKANOL OR OF A MIXTURE OF ACETONE WITH A FORMALDEHYDE PRECURSOR CATALYZED BY A HIGHLY-ACTIVE PD-HCL SYSTEM
CAVINATO, G
TONIOLO, L
[J]. JOURNAL OF MOLECULAR CATALYSIS, 1990, 58 (02): : 251 - 267

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