Pd-catalyzed alkyl to aryl migration and cyclization: An efficient synthesis of fused polycycles via multiple C-H activation

被引:228
作者
Huang, QH [1 ]
Fazio, A [1 ]
Dai, GX [1 ]
Campo, MA [1 ]
Larock, RC [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
关键词
D O I
10.1021/ja047980y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel palladium migration methodology for the synthesis of complex fused polycycles has been developed. This process involves 1,4-palladium alkyl to aryl migrations via through-space C-H activation, followed by intramolecular arylation or an intermolecular Heck reaction providing a very efficient way to synthesize fused ring systems. Copyright © 2004 American Chemical Society.
引用
收藏
页码:7460 / 7461
页数:2
相关论文
共 34 条
[1]   PALLADIUM-CATALYZED C-C BOND FORMATION INVOLVING AROMATIC C-H ACTIVATION .3. ASPECTS OF AROMATIC-SUBSTITUTION AND STRUCTURE OF 1-BROMO-3-[3-(2-METHYLENECYCLOHEX-5-EN-1-YL)BICYCLO[2.2.1]-HEPT-2-YL]-4-BICYCLO[2.2.1]HEPT-2-YLBENZENE [J].
BOCELLI, G ;
CATELLANI, M ;
CHIUSOLI, GP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 279 (1-2) :225-232
[2]   1,4-Palladium migration via C-H activation, followed by arylation: Synthesis of fused polycycles [J].
Campo, MA ;
Huang, QH ;
Yao, TL ;
Tian, QP ;
Larock, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11506-11507
[3]   Novel 1,4-palladium migration in organopalladium intermediates derived from o-iodobiaryis [J].
Campo, MA ;
Larock, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) :14326-14327
[4]  
Cámpora J, 2001, ANGEW CHEM INT EDIT, V40, P3641, DOI 10.1002/1521-3773(20011001)40:19<3641::AID-ANIE3641>3.0.CO
[5]  
2-9
[6]  
Cámpora J, 1999, ANGEW CHEM INT EDIT, V38, P147, DOI 10.1002/(SICI)1521-3773(19990115)38:1/2<147::AID-ANIE147>3.3.CO
[7]  
2-9
[8]   Catalytic multistep reactions via palladacycles [J].
Catellani, M .
SYNLETT, 2003, (03) :298-313
[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]   A novel palladium-catalyzed synthesis of phenanthrenes from ortho-substituted aryl iodides and diphenyl- or alkylphenylacetylenes [J].
Catellani, M ;
Motti, E ;
Baratta, S .
ORGANIC LETTERS, 2001, 3 (23) :3611-3614