Umpolung Reactivity of Indole through Gold Catalysis

被引：203

作者：

Lu, Biao ^{[1
]}

Luo, Yingdong ^{[1
]}

Liu, Lianzhu ^{[1
]}

Ye, Longwu ^{[1
]}

Wang, Yanzhao ^{[1
]}

Zhang, Liming ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 36期

关键词：

catalysis; gold; indole; nitrenes; umpolung; C-H FUNCTIONALIZATION; ONE-POT SYNTHESIS; AROMATIC-COMPOUNDS; EFFICIENT; NUCLEOPHILICITY; HETEROCYCLES; GENERATION; COMPLEXES; INSERTION; CASCADE;

D O I：

10.1002/anie.201103014

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Electrophilic indole? Indoles, which are typically nucleophilic, can be made electrophilic through gold catalysis. By using an ortho-azido group to deliver a nitrene intramolecularly, an arylalkyne is converted into a gold carbene intermediate containing an indole skeleton that is highly electrophilic at the 3-position. A range of functionalized indoles is readily accessed by utilizing this strategy. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8358 / 8362

页数：5

共 65 条

[1]

[Anonymous], 2007, ANGEW CHEM

[2]

[Anonymous], SCI SYNTH

[3]

[Anonymous], 2008, ANGEW CHEM

[4]

Bandini M., 2009, ANGEW CHEM, V121, P9786, DOI DOI 10.1002/ange.200901843

[5] Catalytic Functionalization of Indoles in a New Dimension [J].

Bandini, Marco ;

Eichholzer, Astrid .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644

[6] Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions [J].

Cacchi, Sandro ;

Fabrizi, Giancarlo .

CHEMICAL REVIEWS, 2011, 111 :PR215-PR283

[7]

Carter M., 2008, [No title captured], Patent No. [WO2008058402A1, 2008058402]

[8] Gold(I)-Catalyzed Intermolecular Oxyarylation of Alkynes: Unexpected Regiochemistry in the Alkylatioin of Arenes [J].

Cuenca, Ana B. ;

Montserrat, Sergi ;

Hossain, Kabir M. ;

Mancha, Gisela ;

Lledos, Agusti ;

Medio-Simon, Mercedes ;

Ujaque, Gregori ;

Asensio, Gregorio .

ORGANIC LETTERS, 2009, 11 (21) :4906-4909

[9]

Cui L., 2010, ANGEW CHEM, V122, P9364

[10]

Cui L., 2010, CHEM COMMUN UNPUB

← 1 2 3 4 5 6 7 →