A General Synthesis of Alkenyl-Substituted Benzofurans, Indoles, and Isoquinolones by Cascade Palladium-Catalyzed Heterocyclization/Oxidative Heck Coupling

被引：101

作者：

Alvarez, Rosana ^{[1
]}

Martinez, Claudio ^{[1
]}

Madich, Youssef ^{[2
]}

Denis, J. Gabriel ^{[1
]}

Aurrecoechea, Jose M. ^{[2
]}

de Lera, Angel R. ^{[1
]}

机构：

[1] Univ Vigo, Dept Quim Organ, Fac Quim, Vigo 36310, Spain

[2] Univ Basque Country, Dept Quim Organ 2, Fac Ciencia & Tecnol, E-48080 Bilbao, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 42期

关键词：

cyclization; Heck reaction; heterocycles; homogeneous catalysis; palladium; C-H FUNCTIONALIZATION; FREE NH-INDOLES; BOND FORMATION; O-ALKYNYLPHENOLS; INTRAMOLECULAR CYCLIZATION; EFFICIENT SYNTHESIS; CONJUGATE ADDITION; BASE-FREE; ACIDS; DERIVATIVES;

D O I：

10.1002/chem.201001535

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Structurally diverse C3-alkenylbenzofurans, C3-alkenylindoles, and C4-alkenylisoquinolones are efficiently prepared by using consecutive Sonogashira and cascade Pd-catalyzed heterocyclization/oxidative Heck couplings from readily available ortho-iodosubstituted phenol, aniline, and benzamide substrates, alkynes, and functionalized olefins. The cyclization of O- and N-heteronucleophiles follows regioselec-tive 5-endo-dig- or 6-endo-dig-cyclization modes, whereas the subsequent Heck-type coupling with both mono- and disubstituted olefins takes place stereoselectively with exclusive formation of the E isomers in most cases.

引用

页码：12746 / 12753

页数：8

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