Direct synthesis of highly substituted thiophenes through copper(I)-catalyzed tandem reactions of alkylidenethiiranes with terminal alkynes

被引:15
作者
Zhang, Yiping [1 ]
Bian, Ming [1 ]
Yao, Weijun [1 ]
Gu, Jianming [1 ]
Ma, Cheng [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
基金
中国国家自然科学基金;
关键词
ONE-POT SYNTHESES; MULTICOMPONENT REACTIONS; MOLECULAR DESIGN; CYCLIZATION; HETEROCYCLES; FURANS;
D O I
10.1039/b909284f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel copper(I)-catalyzed tandem addition/cycloisomerization reaction of 1-phenylsulfonylalkylidenethiiranes with terminal alkynes for the convergent assembly of 2-(alpha-phenylsulfonylalkyl)-thiophenes is reported, which could directly assemble various functional groups incorporated into the thiophene ring.
引用
收藏
页码:4729 / 4731
页数:3
相关论文
共 40 条
[1]  
Bertram H. J., 1993, RECENT DEV FLAVOR FR
[2]   The modified Julia olefination:: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds [J].
Blakemore, PR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2563-2585
[3]   PALLADIUM(0)-CATALYZED INTRAMOLECULAR AND INTERMOLECULAR CYCLIZATION REACTIONS OF ALLENE EPISULFIDES [J].
CHOI, N ;
KABE, Y ;
ANDO, W .
TETRAHEDRON LETTERS, 1991, 32 (35) :4573-4576
[4]   Solvent-controlled Csp2→O silyl migration:: The "one-pot" synthesis of 2,3-disubsituted thiophenes [J].
Devarie-Baez, Nelmi O. ;
Shuhler, Brian J. ;
Wang, Hua ;
Xian, Ming .
ORGANIC LETTERS, 2007, 9 (22) :4655-4658
[5]   Multicomponent Type II Anion Relay Chemistry (ARC): One-Pot Syntheses of 2,3-Disubstituted Furans and Thiophenes [J].
Devarie-Baez, Nelmi O. ;
Kim, Won-Suk ;
Smith, Amos B., III ;
Xian, Ming .
ORGANIC LETTERS, 2009, 11 (08) :1861-1864
[6]   Thiazepine moiety-controlled regioselective rearrangements of 7-oxanorbornadiene derivatives [J].
Ding, Hanfeng ;
Zhang, Yiping ;
Yao, Weijun ;
Xu, Duanjun ;
Ma, Cheng .
CHEMICAL COMMUNICATIONS, 2008, (44) :5797-5799
[7]   Concise assembly of highly substituted furan-fused 1,4-thiazepines and their Diels-Alder reactions with benzynes [J].
Ding, Hanfeng ;
Zhang, Yiping ;
Bian, Ming ;
Yao, Weijun ;
Ma, Cheng .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (02) :578-584
[8]   Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis [J].
Evano, Gwilherm ;
Blanchard, Nicolas ;
Toumi, Mathieu .
CHEMICAL REVIEWS, 2008, 108 (08) :3054-3131
[9]   Synthesis of 3,4-bis[(methoxycarbonyl)methyl]thiophene and bis-, ter- and and pentathiophenes with alternating 3,4-bis[(methoxycarbonyl)methyl]-substituted rings [J].
Fazio, A ;
Gabriele, B ;
Salerno, G ;
Destri, S .
TETRAHEDRON, 1999, 55 (02) :485-502
[10]   Tandem catalysis: a taxonomy and illustrative review [J].
Fogg, DE ;
dos Santos, EN .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2365-2379