N-Heterocyclic-Carbene-Catalyzed Synthesis of 2-Aryl Indoles

被引：78
作者：
Hovey, M. Todd [1 ]
Check, Christopher T. [1 ]
Sipher, Alexandra F. [1 ]
Scheidt, Karl A. [1 ]
机构：
[1] Northwestern Univ, Dept Chem, Ctr Mol Innovat & Drug Discovery, Evanston, IL 60208 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 36期
关键词：
asymmetric synthesis; cooperative effects; carbenes; O-QUINONE METHIDES; ACTIVATED DOUBLE-BONDS; ALPHA-ARYL KETONES; N-(ORTHO-CHLOROMETHYL)ARYL AMIDES; ENANTIOSELECTIVE SYNTHESIS; ACYLOIN CONDENSATIONS; INTERNAL ALKYNES; ENOL LACTONES; SULFUR YLIDES; NHC CATALYSIS;
D O I：
10.1002/anie.201405035
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A convergent and efficient transition-metal-free catalytic synthesis of 2-aryl-indoles has been developed. The interception of a highly reactive and transient aza-ortho-quinone methide by an acyl anion equivalent generated through N-hetereocyclic carbene catalysis is central to this successful strategy. High yields and a wide scope as well as the streamlined synthesis of a kinase inhibitor are reported.
引用
收藏
页码：9603 / 9607
页数：5
相关论文
共 108 条
[1]  
[Anonymous], 2012, ANGEW CHEM
[2]  
[Anonymous], 2008, ANGEW CHEM, DOI DOI 10.1002/adsc.200900065
[3]  
[Anonymous], 2010, Angew. Chem
[4]   The aza-xylylene Diels-Alder approach for the synthesis of naturally occurring 2-alkyl tetrahydroquinolines [J].
Avemaria, F ;
Vanderheiden, S ;
Bräse, S .
TETRAHEDRON, 2003, 59 (35) :6785-6796
[5]  
Bandini M., 2009, ANGEW CHEM, V121, P9786, DOI DOI 10.1002/ange.200901843
[6]   Catalytic Functionalization of Indoles in a New Dimension [J].
Bandini, Marco ;
Eichholzer, Astrid .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644
[7]   IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes:: Direct assembly of 3-iodoindole cores [J].
Barluenga, J ;
Trincado, M ;
Rubio, E ;
González, JM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) :2406-2409
[8]  
Barluenga J., 2007, ANGEW CHEM, V119, P1551
[9]  
Barluenga J., 2003, Angew. Chem, V115, P2508
[10]   The azaallylic anion as a synthon for Pd-catalyzed synthesis of heterocycles:: Domino two- and three-component synthesis of indoles [J].
Barluenga, Jose ;
Jimenez-Aquino, Agustin ;
Valdes, Carlos ;
Aznar, Fernando .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1529-1532
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