Palladium-Catalyzed Regioselective Oxidative Coupling of Indoles and One-Pot Synthesis of Acetoxylated Biindolyls

被引:151
作者
Liang, Zuijun [1 ]
Zhao, Jinlong [1 ]
Zhang, Yuhong [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
关键词
DIRECT C-2 ARYLATION; H BOND ARYLATION; DIRECT FUNCTIONALIZATION; ROOM-TEMPERATURE; ARYL BROMIDES; C-O; ACTIVATION; ALDEHYDES; ACID; ALKENYLATION;
D O I
10.1021/jo902265s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mild conditions have been developed to achieve Pd-catalyzed homocoupling of indoles with excellent regioselectivity in the presence of Cu(OAc)(2)center dot H2O in DMSO at room temperature in high efficiency. This method provides a simple route to 2,3-biindolyls from the electron-rich to moderately electron-poor indoles. The reaction tolerates the bromide substitLient on indoles. In addition, a one-pot approach to C3-position acetoxylated biindolyls is realized via palladium catalysis by the use of AgOAc under oxygen atmosphere as oxidants.
引用
收藏
页码:170 / 177
页数:8
相关论文
共 89 条
[1]   Synthesis of 3,3′-disubstituted-2,2′-biindolyls through sequential palladium-catalysed reactions of 2,2,2-trifluoro-N-(2-(4-[2,2,2-trifluoro-acetylamino)-phenyl]-buta-1,3-diynyl)-phenyl)-acetamide with organic halides/triflates [J].
Abbiati, G ;
Arcadi, A ;
Beccalli, E ;
Bianchi, G ;
Marinelli, F ;
Rossi, E .
TETRAHEDRON, 2006, 62 (13) :3033-3039
[2]   Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage [J].
Ackermann, Lutz ;
Novak, Petr ;
Vicente, Ruben ;
Hofmann, Nora .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6045-6048
[3]   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
[4]   Direct palladium-catalyzed C-3 arylation of free (NH)-indoles with aryl bromides under ligandless conditions [J].
Bellina, Fabio ;
Benelli, Francesca ;
Rossi, Renzo .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5529-5535
[5]   Indolocarbazoles [J].
Bergman, J ;
Janosik, T ;
Wahlström, N .
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 80, 2001, 80 :1-71
[6]   Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides [J].
Brasche, Gordon ;
Garcia-Fortanet, Jorge ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2008, 10 (11) :2207-2210
[7]   THE OXIDATIVE ADDITION OF IODOMETHANE TO [PDME2(2,2'-BIPYRIDYL)] AND THE X-RAY STRUCTURE OF THE ORGANOPALLADIUM(IV) PRODUCT FAC-[PDME3(2,2'-BIPYRIDYL)L] [J].
BYERS, PK ;
CANTY, AJ ;
SKELTON, BW ;
WHITE, AH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (23) :1722-1724
[8]   Rational design of 6-methylsulfonylindoles as selective cyclooxygenase-2 inhibitors [J].
Campbell, JA ;
Bordunov, V ;
Broka, CA ;
Browner, MF ;
Kress, JM ;
Mirzadegan, T ;
Ramesha, C ;
Sanpablo, BF ;
Stabler, R ;
Takahara, P ;
Villasenor, A ;
Walker, KAM ;
Wang, JH ;
Welch, M ;
Weller, P .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (18) :4741-4745
[9]   Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes [J].
Campeau, LC ;
Parisien, M ;
Leblanc, M ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9186-9187
[10]   Efficient Synthesis of 5,6-Dihydroxyindole Dimers, Key Eumelanin Building Blocks, by a Unified o-Ethynylaniline-Based Strategy for the Construction of 2-Linked Biindolyl Scaffolds [J].
Capelli, Luigia ;
Manini, Paola ;
Pezzella, Alessandro ;
Napolitano, Alessandra ;
d'Ischia, Marco .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (18) :7191-7194