Co(I)- versus Ru(II)-Catalyzed [2+2+2] cycloadditions involving alkynyl halides

被引：14

作者：

Iannazzo, Laura ^{[2
]}

Kotera, Naoko ^{[2
]}

Malacria, Max ^{[2
]}

Aubert, Corinne ^{[2
]}

Gandon, Vincent ^{[1
,2
]}

机构：

[1] Univ Paris 11, ICMMO, CNRS, UMR 8182, F-91405 Orsay, France

[2] UPMC Univ Paris 06, Inst Parisien Chim Mol, UMR CNRS 7201 FR 2769, F-75005 Paris, France

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2011年 / 696卷 / 24期

关键词：

Alkynes; Catalysis; Cobalt; Cycloadditions; Ruthenium; RUTHENIUM-CATALYZED CYCLOADDITION; SPOROLIDE B; COBALT; CYCLIZATIONS; ANTIBIOTICS; COMPLEXES; DIYNES;

D O I：

10.1016/j.jorganchem.2011.08.041

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Alkynyl chlorides, bromides, and iodides have been tested as [2 + 2 + 2] cycloaddition partners using CpCo(CO)(dimethylfumarate) and Cp*Ru(cod)Cl as precatalysts. A series of cocyclizations between diynyl dihalides and alkynes, as well as intramolecular cycloadditions of triynyl dihalides, has been carried out. While this study confirmed the versatility of the ruthenium complex with all kinds of halides, the cheap air-stable cobalt complex proved nonetheless efficient with alkynyl bromides. (C) 2011 Elsevier B.V. All rights reserved.

引用

页码：3906 / 3908

页数：3

共 26 条

[1]

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

[2] Alkynyl halides in ruthenium(II)-catalyzed [2+2] cycloadditions of bicyclic alkenes [J].

Allen, Anna ;

Villeneuve, Karine ;

Cockburn, Neil ;

Fatila, Elisabeth ;

Riddell, Nicole ;

Tam, William .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (24) :4178-4192

[3] Tandem aminocarbonylation/Pauson-Khand reaction of haloacetylenes [J].

Balsells, J ;

Moyano, A ;

Riera, A ;

Pericàs, MA .

ORGANIC LETTERS, 1999, 1 (12) :1981-1984

[4] [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

[5] TRANSITION-METAL-CATALYZED ALKYNE CYCLIZATIONS - A COBALT-MEDIATED TOTAL SYNTHESIS OF DL-ESTRONE [J].

FUNK, RL ;

VOLLHARDT, KPC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (16) :5253-5261

[6]

GANDON V, 2008, E EROS, DOI DOI 10.1002/047084289X.RN00943.PUB2

[7] Recent progress in cobalt-mediated [2+2+2] cycloaddition reactions [J].

Gandon, Vincent ;

Aubert, Corinne ;

Malacria, Max .

CHEMICAL COMMUNICATIONS, 2006, (21) :2209-2217

[8] Air-Stable {(C5H5)Co} Catalysts for [2+2+2] Cycloadditions [J].

Geny, Anais ;

Agenet, Nicolas ;

Iannazzo, Laura ;

Malacria, Max ;

Aubert, Corinne ;

Gandon, Vincent .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (10) :1810-1813

[9] Intramolecular Rhodium-Catalyzed [2+2+2] Cyclizations of Diynes with Enones [J].

Jones, Amanda L. ;

Snyder, John K. .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (07) :2907-2910

[10] The Cobalt Way to Angucyclinones: Asymmetric Total Synthesis of the Antibiotics (+)-Rubiginone B2, (-)-Tetrangomycin, and (-)-8-O-Methyltetrangomycin [J].

Kesenheimer, Christian ;

Kalogerakis, Aris ;

Meissner, Anja ;

Groth, Ulrich .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (29) :8805-8821

← 1 2 3 →