Beyond Reppe: Building Substituted Arenes by [2+2+2] Cycloadditions of Alkynes

被引：258

作者：

Galan, Brandon R. ^{[1
]}

Rovis, Tomislav ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 16期

关键词：

arenes; cycloaddition; homogeneous catalysis; multicomponent reactions; REGIOSELECTIVE INTERMOLECULAR CYCLOTRIMERIZATION; CATIONIC RHODIUM(I)/MODIFIED BINAP; ONE-POT SYNTHESIS; BENZENE-DERIVATIVES; ORGANIC-SYNTHESIS; COMPLEXES; CONSTRUCTION; CATALYST; ACETYLENES; EFFICIENT;

D O I：

10.1002/anie.200804651

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Synthetic sequel: The transition-metal-catalyzed [2+2+2] cycloaddition is an established method for the construction of carbocyclic frameworks but is often plagued by poor selectivity. Recent literature paints a promising picture - a more general metal-catalyzed [2+2+2] cycloaddition can be accomplished intermolecularly using three separate alkynes to furnish highly substituted arenas (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2830 / 2834

页数：5

共 35 条

[1]

Agenet N., 2007, ORG REACT, V68, P1

[2] One-pot synthesis of benzolactones and lactams via a cobalt-catalyzed regioselective [2+2+2] cocyclotrimerization of alkynyl alcohols and amines with propiolates [J].

Chang, HT ;

Jeganmohan, M ;

Cheng, CH .

CHEMICAL COMMUNICATIONS, 2005, (39) :4955-4957

[3] [2+2+2] cycloaddition reactions catalyzed by transition metal complexes [J].

Chopade, Pramod R. ;

Louie, Janis .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2307-2327

[4] Efficient activation of 2-Iminomethylpyridine/Cobalt-Based alkyne [2+2+2}cycloaddition catalyst by addition of a silver salt [J].

Goswami, Avijit ;

Itoa, Taichi ;

Okamoto, Sentaro .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (14-15) :2368-2374

[5] Liquid enol ethers and acetates as gaseous alkyne equivalents in Rh-catalyzed chemo- and regioselective formal cross-alkyne cyclotrimerization [J].

Hara, Hirorni ;

Hirano, Masao ;

Tanaka, Ken .

ORGANIC LETTERS, 2008, 10 (12) :2537-2540

[6] The fascinating construction of pyridine ring systems by transition metal-catalysed [2+2+2] cycloaddition reactions [J].

Heller, Barbara ;

Hapke, Marko .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1085-1094

[7] De novo synthesis of substituted pyridines [J].

Henry, GD .

TETRAHEDRON, 2004, 60 (29) :6043-6061

[8] Ligand and solvent effects on cobalt(I)-catalysed reactions: Alkyne dimerisation versus [2+2+2]-cyclotrimerisation versus Diels-Alder reaction versus [4+2+2]-cycloaddition [J].

Hilt, G ;

Hess, W ;

Vogler, T ;

Hengst, C .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (23) :5170-5181

[9] A simple cobalt catalyst system for the efficient and regioselective cyclotrimerisation of alkynes [J].

Hilt, G ;

Vogler, T ;

Hess, W ;

Galbiati, F .

CHEMICAL COMMUNICATIONS, 2005, (11) :1474-1475

[10] Solvent-dependent regiochemical cyclotrimerisation of phenylacetylene with cobalt catalysts containing disulfide ligands: A case study [J].

Hilt, Gerhard ;

Hengst, Christoph ;

Hess, Wilfried .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (13) :2293-2297

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