CuBr-Catalyzed Coupling of N-Tosylhydrazones and Terminal Alkynes: Synthesis of Benzofurans and Indoles

被引：158
作者：
Zhou, Lei
Shi, Yi
Xiao, Qing
Liu, Yizhou
Ye, Fei
Zhang, Yan
Wang, Jianbo [1 ]
机构：
[1] Peking Univ, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 05期
基金：
中国国家自然科学基金; 中国博士后科学基金;
关键词：
ENDO-MODE CYCLIZATION; ACETYLENIC-COMPOUNDS; EFFICIENT SYNTHESIS; O-IODOPHENOLS; VINYL IODIDES; COPPER-FREE; ARYL; HETEROCYCLES; DERIVATIVES; HETEROANNULATION;
D O I：
10.1021/ol103009n
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new method for the synthesis of benzofurans or indoles via ligand-free CuBr-catalyzed coupling/cyclization of terminal alkynes with N-tosylhydrazones derived from o-hydroxy- or o-aminobenzaldehydes has been developed. A wide range of functional groups were found that are able to tolerate the reaction conditions.
引用
收藏
页码：968 / 971
页数：4
相关论文
共 44 条
[1]   Pd-catalyzed cross-coupling reactions with carbonyls:: Application in a very efficient synthesis of 4-aryltetrahydropyridines [J].
Barluenga, Jose ;
Tomas-Gamasa, Maria ;
Moriel, Patricia ;
Amar, Fernando ;
Valdes, Carlos .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) :4792-4795
[2]   N-tosylhydrazones as reagents for cross-coupling reactions:: A route to polysubstituted olefins [J].
Barluenga, José ;
Moriel, Patricia ;
Valdes, Carlos ;
Aznar, Fernando .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5587-5590
[3]   Synthesis of Enol Ethers and Enamines by Pd-Catalyzed Tosylhydrazide-Promoted Cross-Coupling Reactions [J].
Barluenga, Jose ;
Escribano, Maria ;
Moriel, Patricia ;
Aznar, Fernando ;
Valdes, Carlos .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (48) :13291-13294
[4]   Synthesis of 2-arylbenzo[b]furans via copper(I)-catalyzed coupling of o-iodophenols and aryl acetylenes [J].
Bates, CG ;
Saejueng, P ;
Murphy, JM ;
Venkataraman, D .
ORGANIC LETTERS, 2002, 4 (26) :4727-4729
[5]   Efficient synthesis of 5-nitro-benzo[b]furans via 2-bromo-4-nitro-phenyl acetates [J].
Bochicchio, Antonella ;
Chiummiento, Lucia ;
Funicello, Maria ;
Lopardo, Maria Teresa ;
Lupattelli, Paolo .
TETRAHEDRON LETTERS, 2010, 51 (21) :2824-2827
[6]   Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].
Cacchi, S ;
Fabrizi, G .
CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920
[7]  
Cagniant P., 1975, ADV HETEROCYCL CHEM, V18, P343
[8]   Sonogashira cross-coupling reactions catalysed by copper-free palladium zeolites [J].
Djakovitch, L ;
Rollet, P .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1782-1792
[9]  
Donnelly D.M. X., 1984, Comprehensive Heterocyclic Chemistry, V4, P657
[10]  
Gribble G.W., 1996, COMPREHENSIVE HETERO, V2, P207, DOI DOI 10.1016/B978-008096518-5.00043-5
12345