Room-temperature AuI-catalyzed C-C bond formation through a tandem Friedel-Crafts-type addition/carbocyclization reaction

被引：147
作者：
Toullec, Patrick Yves [1 ]
Genin, Emilie [1 ]
Leseurre, Lucie [1 ]
Genet, Jean-Pierre [1 ]
Michelet, Veronique [1 ]
机构：
[1] Ecole Natl Super Chim Paris, Lab Synth Select Organ & Prod Nat, UMR 7573, F-75231 Paris 05, France
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 44期
关键词：
arenes; C-H activation; cyclization; gold; tandem reaction;
D O I：
10.1002/anie.200601980
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) A golden tandem reaction: The [PPh 3AuCl]/AgSbF6 catalytic system promotes a tandem reaction composed of a Friedel-Crafts-type addition of electron-rich aromatic and heteroaromatic derivatives to unactivated alkenes and a carbocyclization (see scheme; Z = C(CO2Me)2, C(SO2Ph)2, O, NTs). The reaction is compatible with various functional groups on the enynes and nucleophiles, and proceeds rapidly at room temperature. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
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收藏
页码：7427 / 7430
页数：4
相关论文
共 67 条
[1]   Gold-catalyzed C-3-alkylation of 7-azaindoles through Michael-type addition to α,β-enones [J].
Alfonsi, Maria ;
Arcadi, Antonio ;
Bianchi, Gabriele ;
Marinelli, Fabio ;
Nardini, Antonella .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (10) :2393-2402
[2]   Origins, current status, and future challenges of green chemistry [J].
Anastas, PT ;
Kirchhoff, MM .
ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) :686-694
[3]  
[Anonymous], 2005, ANGEW CHEM, V117, P7150, DOI DOI 10.1002/ANGE.200502735
[4]   Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols [J].
Antoniotti, S ;
Genin, E ;
Michelet, V ;
Genêt, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9976-9977
[5]   Recent applications of gold catalysis in organic synthesis [J].
Arcadi, A ;
Di Giuseppe, S .
CURRENT ORGANIC CHEMISTRY, 2004, 8 (09) :795-812
[6]   Gold-catalysed direct couplings of indoles and pyrroles with 1,3-dicarbonyl compounds [J].
Arcadi, A ;
Alfonsi, M ;
Bianchi, G ;
D'Anniballe, G ;
Marinelli, F .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (03) :331-338
[7]   Gold-catalyzed conjugate addition type reaction of indoles with α,β-enones [J].
Arcadi, A ;
Bianchi, G ;
Chiarini, M ;
D'anniballe, G ;
Marinelli, F .
SYNLETT, 2004, (06) :944-950
[8]   SELECTIVE INTERMOLECULAR CARBON-HYDROGEN BOND ACTIVATION BY SYNTHETIC METAL-COMPLEXES IN HOMOGENEOUS SOLUTION [J].
ARNDTSEN, BA ;
BERGMAN, RG ;
MOBLEY, TA ;
PETERSON, TH .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) :154-162
[9]  
BIANCHI G, 2004, TARGETS HETEROCYCLIC, V8, P82
[10]   Functionalized carbo- and heterocycles via Pt-catalyzed asymmetric alkoxycyclization of 1,6-enynes [J].
Charruault, L ;
Michelet, V ;
Taras, R ;
Gladiali, S ;
Genêt, JP .
CHEMICAL COMMUNICATIONS, 2004, (07) :850-851
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