Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles

被引：18

作者：

Alvarez, Estela ^{[1
]}

Miguel, Delia ^{[1
]}

Garcia-Garcia, Patricia ^{[1
]}

Fernandez-Rodriguez, Manuel A. ^{[1
]}

Rodriguez, Felix ^{[2
]}

Sanz, Roberto ^{[1
]}

机构：

[1] Univ Burgos, Dept Quim, Fac Ciencias, Area Quim Organ, Burgos 09001, Spain

[2] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, E-33006 Oviedo, Spain

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 7卷

关键词：

catalysis; gold; indoles; Nazarov cyclizations; selectivity; GOLD CATALYSIS; 1,2-INDOLE MIGRATIONS; INDOLES; REACTIVITY; ACCESS;

D O I：

10.3762/bjoc.7.89

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selectivity of our previously described gold-catalyzed tandem reaction, 1,2-indole migration followed by aura-iso-Nazarov cyclization, of 3-propargylindoles bearing (hetero) aromatic substituents at both the propargylic and terminal positions, was reversed by the proper choice of the catalyst and the reaction conditions. Thus, 3-(inden-2-yl) indoles, derived from an aura-Nazarov cyclization (instead of an aura-iso-Nazarov cyclization), were obtained in moderate to good yields from a variety of 3-propargylindoles.

引用

页码：786 / 793

页数：8

共 28 条

[1] Steering the Surprisingly Modular π-Acceptor Properties of N-Heterocyclic Carbenes: Implications for Gold Catalysis [J].

Alcarazo, Manuel ;

Stork, Timon ;

Anoop, Anakuthil ;

Thiel, Walter ;

Fuerstner, Alois .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (14) :2542-2546

[2] Gold-catalyzed decorations of arenes and heteroarenes with C-C multiple bonds [J].

Bandini, Marco .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (03) :1358-1367

[3] Gold(I)-catalyzed divergence in the reactivity of 3-silyloxy 1,6-enynes: Pinacol-terminated vs claisen-terminated cyclization cascades [J].

Baskar, Baburaj ;

Bae, Hyo J. ;

An, Sang E. ;

Cheong, Jae Y. ;

Rhee, Young H. ;

Duschek, Alexander ;

Kirsch, Stefan F. .

ORGANIC LETTERS, 2008, 10 (12) :2605-2607

[4] Carbo- and heterocyclisation of oxygen- and nitrogen-containing electrophiles by platinum, gold, silver and copper species [J].

Das, Arindam ;

Abu Sohel, Shariar Md. ;

Liu, Rai-Shung .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (05) :960-979

[5] Counterion Effects in a Gold-Catalyzed Synthesis of Pyrroles from Alkynyl Aziridines [J].

Davies, Paul W. ;

Martin, Nicolas .

ORGANIC LETTERS, 2009, 11 (11) :2293-2296

[6] Computation-Guided Development of Au-Catalyzed Cycloisomerizations Proceeding via 1,2-Si or 1,2-H Migrations: Regiodivergent Synthesis of Silylfurans [J].

Dudnik, Alexander S. ;

Xia, Yuanzhi ;

Li, Yahong ;

Gevorgyan, Vladimir .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (22) :7645-7655

[7] Intra- and intermolecular reactions of indoles with alkynes catalyzed by gold [J].

Ferrer, Catalina ;

Amijs, Catelijne H. M. ;

Echavarren, Antonio M. .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (05) :1358-1373

[8] Gold and platinum catalysis-a convenient tool for generating molecular complexity [J].

Fuerstner, Alois .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3208-3221

[9] Ligand effects in homogeneous Au catalysis [J].

Gorin, David J. ;

Sherry, Benjamin D. ;

Toste, F. Dean .

CHEMICAL REVIEWS, 2008, 108 (08) :3351-3378

[10] Gold-catalyzed cycloisomerizations of enynes:: A mechanistic perspective [J].

Jimenez-Nunez, Eloisa ;

Echavarren, Antonio M. .

CHEMICAL REVIEWS, 2008, 108 (08) :3326-3350

← 1 2 3 →