Tandem Palladium-Catalyzed N,C-Coupling/Carbonylation Sequence for the Synthesis of 2-Carboxyindoles

被引:96
作者
Vieira, Tiago O. [1 ]
Meaney, Laura A. [1 ]
Shi, Yong-Ling [1 ]
Alper, Howard [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1021/ol801985q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tandem palladium-catalyzed N,C-coupling/carbonylation, under 10 atm of carbon monoxide and at 110 degrees C, is a novel and efficient method for the preparation of 2-carboxyindoles. The catalyst system tolerates a variety of functional groups, and the noted indoles were obtained in good isolated yields.
引用
收藏
页码:4899 / 4901
页数:3
相关论文
共 48 条
[1]   A novel one-pot synthesis of N-acylindoles from primary aromatic amides [J].
Abid, Mohammed ;
De Paolis, Omar ;
Toeroek, Bela .
SYNLETT, 2008, (03) :410-412
[2]  
[Anonymous], SCI SYNTHESIS
[3]   Cu(I)-catalyzed intramolecular cyclization of ene-carbamates:: synthesis of indoles and pyrrolo[2,3-c]pyridines [J].
Barberis, C ;
Gordon, TD ;
Thomas, C ;
Zhang, XL ;
Cusack, KP .
TETRAHEDRON LETTERS, 2005, 46 (51) :8877-8880
[4]   Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].
Cacchi, S ;
Fabrizi, G .
CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920
[5]   Regioselective and versatile synthesis of indoles via intramolecular Friedel-Crafts heteroannulation of enaminones [J].
Cruz, MD ;
Jiménez, F ;
Delgado, F ;
Tamariz, J .
SYNLETT, 2006, (05) :749-755
[6]   Synthesis and transformations of ethyl 3-(Benzoylamino)-1H-indole-2-carboxylates [J].
Cucek, Karmen ;
Vercek, Bojan .
SYNTHESIS-STUTTGART, 2008, (11) :1741-1746
[7]   New arylthioindoles: Potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies [J].
De Martino, G ;
Edler, MC ;
La Regina, G ;
Coluccia, A ;
Barbera, MC ;
Barrow, D ;
Nicholson, RI ;
Chiosis, G ;
Brancale, A ;
Hamel, E ;
Artico, M ;
Silvestri, R .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (03) :947-954
[8]   Pd-catalyzed tandem C-N/C-C coupling of gem-dihalovinyl systems: A modular synthesis of 2-substituted indoles [J].
Fang, YQ ;
Lautens, M .
ORGANIC LETTERS, 2005, 7 (16) :3549-3552
[9]   A highly selective tandem cross-coupling of gem-dihaloolefins for a modular, efficient synthesis of highly functionalized indoles [J].
Fang, Yuan-Qing ;
Lautens, Mark .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (02) :538-549
[10]   Synthesis of 2-vinylic indoles and derivatives via a Pd-catalyzed tandem coupling reaction [J].
Fayol, Aude ;
Fang, Yuan-Qing ;
Lautens, Mark .
ORGANIC LETTERS, 2006, 8 (19) :4203-4206