A Direct Palladium-Catalyzed Route to Selectively Substituted Carbazoles through Sequential C-C and C-N Bond Formation: Synthesis of Carbazomycin A

被引:78
作者
Della Ca, Nicola [1 ,2 ]
Sassi, Giovanni [1 ,2 ]
Catellani, Marta [1 ,2 ]
机构
[1] Univ Parma, Dipartimento Chim Organ & Ind, I-43100 Parma, Italy
[2] Univ Parma, CIRCC, I-43100 Parma, Italy
关键词
carbazoles; catalysis; C-H activation; norbornene; palladium;
D O I
10.1002/adsc.200800421
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The present paper offers a synthetically simple one-pot procedure for the catalytic preparation of the biologically interesting class of carbazoles. The new procedure is based on the combined catalysis of palladium and norbornene starting from o-substituted iodoarenes and N-sulfonylated or N-acetylated o-bromoanilines. A well-known member of this class, carbazomycin A, has been successfully prepared.
引用
收藏
页码:2179 / 2182
页数:4
相关论文
共 44 条
[1]   Domino N-H/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes [J].
Ackermann, Lutz ;
Althammer, Andreas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1627-1629
[2]   A novel catalytic one-pot synthesis of carbazoles via consecutive amination and C-H activation [J].
Bedford, RB ;
Cazin, CSJ .
CHEMICAL COMMUNICATIONS, 2002, (20) :2310-2311
[3]   N-H carbazole synthesis from 2-chloroanilines via consecutive amination and C-H activation [J].
Bedford, Robin B. ;
Betham, Michael .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) :9403-9410
[4]   Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].
Campeau, LC ;
Parisien, M ;
Jean, A ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590
[5]   Aryl to aryl palladium migration in the Heck and Suzuki coupling of o-halobiaryls [J].
Campo, Marino A. ;
Zhang, Haiming ;
Yao, Tuanli ;
Ibdah, Abdellatif ;
McCulla, Ryan D. ;
Huang, Qinhua ;
Zhao, Jian ;
Jenks, William S. ;
Larock, Richard C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (19) :6298-6307
[6]   DEVELOPMENT OF ORGANOPALLADIUM(IV) CHEMISTRY - FUNDAMENTAL-ASPECTS AND SYSTEMS FOR STUDIES OF MECHANISM IN ORGANOMETALLIC CHEMISTRY AND CATALYSIS [J].
CANTY, AJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (02) :83-90
[7]  
Catellani M, 2005, TOP ORGANOMETAL CHEM, V14, P21
[8]   PALLADIUM-(II) AND PALLADIUM-(IV) COMPLEXES AS INTERMEDIATES IN CATALYTIC C-C BOND-FORMING REACTIONS [J].
CATELLANI, M ;
CHIUSOLI, GP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 346 (01) :C27-C30
[9]   Palladium-arene interactions in catalytic intermediates:: An experimental and theoretical investigation of the soft rearrangement between η1 and η2 coordination modes [J].
Catellani, M ;
Mealli, C ;
Motti, E ;
Paoli, P ;
Perez-Carreño, E ;
Pregosin, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (16) :4336-4346
[10]   PALLADACYCLE FORMATION BY ELECTROPHILIC AROMATIC-SUBSTITUTION, AS MONITORED BY H-1-NMR SPECTROSCOPY [J].
CATELLANI, M ;
CHIUSOLI, GP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 425 (1-2) :151-154