N-H carbazole synthesis from 2-chloroanilines via consecutive amination and C-H activation

被引:162
作者
Bedford, Robin B. [1 ]
Betham, Michael [1 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1021/jo061749g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-H carbazoles can be produced from 2-chloroanilines and aryl bromides via consecutive catalytic amination and C-H activation. In many instances, this can be done in a tandem manner in one pot. The methodologies developed can be used in the synthesis of a range of carbazoles, including the natural products Clausine P and glycozolidine and a precursor in the synthesis of Clausines H, K, O, and 7-methoxy-O-methylmukonal, and can be extended to the synthesis of indoles.
引用
收藏
页码:9403 / 9410
页数:8
相关论文
共 43 条
[1]   Phosphine oxides as preligands in ruthenium-catalyzed arylations via C-H bond functionalization using aryl chlorides [J].
Ackermann, L .
ORGANIC LETTERS, 2005, 7 (14) :3123-3125
[2]   PALLADIUM-CATALYZED CYCLIZATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION [J].
AMES, DE ;
OPALKO, A .
TETRAHEDRON, 1984, 40 (10) :1919-1925
[3]   SOME REACTIONS OF 3-HALOGENOCINNOLINES CATALYZED BY PALLADIUM COMPOUNDS [J].
AMES, DE ;
BULL, D .
TETRAHEDRON, 1982, 38 (03) :383-387
[4]  
AMES DE, 1983, SYNTHESIS, V235
[5]   Cascade alkenyl amination/heck reaction promoted by a bifunctional palladium catalyst:: A novel one-pot synthesis of indoles from o-haloanilines and alkenyl halides [J].
Barluenga, J ;
Fernández, MA ;
Aznar, F ;
Valdés, C .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) :2276-2283
[6]   The development of palladium catalysts for C-C and C-heteroatom bond forming reactions of aryl chloride substrates [J].
Bedford, RB ;
Cazin, CSJ ;
Holder, D .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2283-2321
[7]   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
[8]   ACETOGENIC ISOQUINOLINE ALKALOIDS .17. 1ST TOTAL SYNTHESIS OF (-)-DIONCOPHYLLINE-A (TRIPHYOPHYLLINE) AND OF SELECTED STEREOISOMERS - COMPLETE (REVISED) STEREOSTRUCTURE [J].
BRINGMANN, G ;
JANSEN, JR ;
REUSCHER, H ;
RUBENACKER, M ;
PETERS, K ;
VONSCHNERING, HG .
TETRAHEDRON LETTERS, 1990, 31 (05) :643-646
[9]   Nondynamic and dynamic kinetic resolution of lactones with stereogenic centers and axes: Stereoselective total synthesis of herbertenediol and mastigophorenes A and B [J].
Bringmann, G ;
Pabst, T ;
Henschel, P ;
Kraus, J ;
Peters, K ;
Peters, EM ;
Rycroft, DS ;
Connolly, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9127-9133
[10]   THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].
BRINGMANN, G ;
WALTER, R ;
WEIRICH, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991