Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6-and 6/5/5/6-heterocyclic systems

被引:60
作者
Chernyak, Natalia [1 ]
Tilly, David [1 ]
Li, Zhou [1 ]
Gevorgyan, Vladimir [1 ]
机构
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
基金
美国国家卫生研究院;
关键词
ROOM-TEMPERATURE; DIRECT ARYLATION; CYCLIZATION; HETEROCYCLES; ALKALOIDS; MECHANISM; INDOLES; ROUTE;
D O I
10.1039/b919991h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Polycyclic indole structures, possessing fused seven-membered rings were efficiently synthesized via the Pd-catalyzed intramolecular carbopalladation-annulation of 3-(2-iodobenzyl)-indoles and alkynes. A remarkable base effect on the chemoselectivity of this transformation has been found: switching from Et3N to CsOAc completely reverses the reaction path to intramolecular cyclization forming fused five-membered rings.
引用
收藏
页码:150 / 152
页数:3
相关论文
共 28 条
[1]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[2]   New cascade 2-indolylacyl radical addition-cyclization reactions [J].
Bennasar, ML ;
Roca, T ;
Griera, R ;
Bosch, J .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22) :7547-7551
[3]   A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction [J].
Bressy, C ;
Alberico, D ;
Lautens, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13148-13149
[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]   Synthesis of fluoren-9-ones by the palladium-catalyzed cyclocarbonylation of o-halobiaryls [J].
Campo, MA ;
Larock, RC .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5616-5620
[6]   Palladium-catalyzed arylation of electron-rich heterocycles with aryl chlorides [J].
Chiong, Hendrich A. ;
Daugulis, Olafs .
ORGANIC LETTERS, 2007, 9 (08) :1449-1451
[7]   Direct Pd-catalyzed arylation of 1,2,3-triazoles [J].
Chuprakov, Stepan ;
Chernyak, Natalia ;
Dudnik, Alexander S. ;
Gevorgyan, Vladimir .
ORGANIC LETTERS, 2007, 9 (12) :2333-2336
[8]   Regioselective synthesis of substituted pyrroles: Efficient palladium-catalyzed cyclization of internal alkynes and 2-amino-3-iodoacrylate derivatives [J].
Crawley, Matthew L. ;
Goljer, Igor ;
Jenkins, Douglas J. ;
Mehlmann, John F. ;
Nogle, Lisa ;
Dooley, Rebecca ;
Mahaney, Paige E. .
ORGANIC LETTERS, 2006, 8 (25) :5837-5840
[9]   Room temperature palladium-catalyzed 2-arylation of indoles [J].
Deprez, NR ;
Kalyani, D ;
Krause, A ;
Sanford, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :4972-4973
[10]   Radical cyclisation reactions with indoles [J].
Flanagan, SR ;
Harrowven, DC ;
Bradley, M .
TETRAHEDRON LETTERS, 2003, 44 (09) :1795-1798