Palladium-catalyzed carbonylation of haloindoles:: No need for protecting groups

被引:73
作者
Kumar, K
Zapf, A
Michalik, D
Tillack, A
Heinrich, T
Böttcher, H
Arlt, M
Beller, M
机构
[1] Univ Rostock, Leibniz Inst Organ Katalyse, D-18055 Rostock, Germany
[2] E Merck AG, D-64293 Darmstadt, Germany
关键词
D O I
10.1021/ol035988r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
For the first time, palladium-catalyzed carbonylations of unprotected bromoindoles have been performed successfully with different N- and O-nucleophiles. Various indole carboxylic acid derivatives are accessible in excellent yield. For example, aminocarbonylation of 4-, 5-, 6-, or 7-bromoindole with arylethylpiperazines provides a direct one-step synthesis for CNS active amphetamine derivatives.
引用
收藏
页码:7 / 10
页数:4
相关论文
共 47 条
[1]  
AKGUN H, 1988, J PHARM SCI, V17, P735
[2]   EMD 281014, a new selective serotonin 5-HT2A receptor antagonist [J].
Bartoszyk, GD ;
van Amsterdam, C ;
Böttcher, H ;
Seyfried, CA .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2003, 473 (2-3) :229-230
[3]   Base-catalyzed amination of olefins: an example of an environmentally friendly synthesis of amines [J].
Beller, M ;
Breindl, C .
CHEMOSPHERE, 2001, 43 (01) :21-26
[4]  
Beller M, 2001, CHIMIA, V55, P684
[5]  
Beller M, 1998, ANGEW CHEM INT EDIT, V37, P3389, DOI 10.1002/(SICI)1521-3773(19981231)37:24<3389::AID-ANIE3389>3.0.CO
[6]  
2-D
[7]  
Beller M, 2001, SYNTHESIS-STUTTGART, P1098, DOI 10.1055/s-2001-14576
[8]   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
[9]   Anti-Markovnikov-functionalizations of unsaturated compounds part 3 - Base-catalyzed hydroamination of aromatic olefins - An efficient route to 1-aryl-4-(arylethyl)piperazines [J].
Beller, M ;
Breindl, C .
TETRAHEDRON, 1998, 54 (23) :6359-6368
[10]  
Beller M., 1998, ANGEW CHEM, V110, P3571