Combined C-H functionalization/C-N bond formation route to carbazoles

被引:657
作者
Tsang, WCP [1 ]
Zheng, N [1 ]
Buchwald, SL [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ja055353i
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new method in which a series of substituted carbazoles is efficiently produced by the combination of an amide and an arene is described. The key feature of this method is the palladium-catalyzed tandem directed C-H functionalization and amide arylation. The method tolerates substitution on either ring of the biaryl amide substrates, and the products can be assembled in a simple two-step protocol from readily available reagents. The Pd(0) species generated are reoxidized to Pd(II) in the presence of Cu(OAc)2 and an atmosphere of oxygen. Copyright © 2005 American Chemical Society.
引用
收藏
页码:14560 / 14561
页数:2
相关论文
共 36 条
[1]  
[Anonymous], 2005, NAME REACTIONS HETER
[2]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[3]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[4]   Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].
Boele, MDK ;
van Strijdonck, GPF ;
de Vries, AHM ;
Kamer, PCJ ;
de Vries, JG ;
van Leeuwen, PWNM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587
[5]   Aerobic oxidative amination of unactivated alkenes catalyzed by palladium [J].
Brice, JL ;
Harang, JE ;
Timokhin, VI ;
Anastasi, NR ;
Stahl, SS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) :2868-2869
[6]  
Brown E. G., 1998, RING NITROGEN KEY BI
[7]  
Chakraborty D.P., 1993, The Alkaloids, V44, P257
[8]   C-C bond formation via C-H bond activation: Synthesis of the core of teleocidin B4 [J].
Dangel, BD ;
Godula, K ;
Youn, SW ;
Sezen, B ;
Sames, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) :11856-11857
[9]   Anilide ortho-arylation by using C-H activation methodology [J].
Daugulis, O ;
Zaitsev, VG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) :4046-4048
[10]  
DAVIES HML, 2005, ANGEW CHEM, V44, P2