Important consequences for gas chromatographic analysis of the Sonogashira cross-coupling reaction

被引：18

作者：

Niemelä, EH ^{[1
]}

Lee, AF ^{[1
]}

Fairlamb, IJS ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 18期

关键词：

palladium; sonogashira; cross-coupling reactions; 2-pyrones;

D O I：

10.1016/j.tetlet.2004.03.060

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

On following the kinetics of the Sonogashira alkynylation reaction of halogenated 2-pyrone 1 with phenylacetylene we have found that turnover continues to occur in sample vials even after quenching by commonly employed silica adsorption methods and product elution with small quantities of CH2Cl2. Trace quantities of Pd are carried through the silica plug. Addition of a CH2Cl2 solution of 1,2-bis(diphenylphosphino)ethane (dppe) to the quenched sample inhibits the reaction and represents a more reliable method for determining yields and reaction kinetics. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3593 / 3595

页数：3

共 18 条

[1] Synthesis of (Bromo-η4-2-pyrone)tricarbonyliron complexes [J].

Fairlamb, IJS ;

Syvänne, SM ;

Whitwood, AC .

SYNLETT, 2003, (11) :1693-1697

[2] Palladium-catalysed alkynylations of 2-pyrone (pyran-2-one) halides [J].

Fairlamb, IJS ;

Lu, FJ ;

Schmidt, JP .

SYNTHESIS-STUTTGART, 2003, (16) :2564-2570

[3] Palladium-tetraphosphine complex: an efficient catalyst for the coupling of aryl halides with alkynes [J].

Feuerstein, M ;

Berthiol, F ;

Doucet, H ;

Santelli, M .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (13) :2235-2237

[4]

HECK RF, 1995, PALLADIUM REAGENTS O

[5] Continuous biphasic catalysis: palladium catalyzed cross coupling reactions [J].

Hillerich, J ;

Plenio, H .

CHEMICAL COMMUNICATIONS, 2003, (24) :3024-3025

[6] A versatile catalyst for the Sonogashira coupling of aryl chlorides [J].

Köllhofer, A ;

Pullmann, T ;

Plenio, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (09) :1056-+

[7] Suzuki cross-coupling approaches to the synthesis of bioactive 3-substituted and 5-substituted-4-methoxy-6-methyl-2-pyrones [J].

Marrison, LR ;

Dickinson, JM ;

Fairlamb, IJS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (16) :2667-2671

[8] Bioactive 4-substituted-6-methyl-2-pyrones with promising cytotoxicity against A2780 and K562 cell lines [J].

Marrison, LR ;

Dickinson, JM ;

Fairlamb, IJS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (24) :3509-3513

[9] An efficient synthesis of 4-alkenyl/alkynyl-6-methyl-2-pyrones via Pd-catalysed coupling on 4-bromo-6-methyl-2-pyrone [J].

Marrison, LR ;

Dickinson, JM ;

Ahmed, R ;

Fairlamb, IJS .

TETRAHEDRON LETTERS, 2002, 43 (49) :8853-8857

[10] Improved sonogashira C-C coupling through clay supported palladium complexes with tridentate pincer bis-carbene ligands [J].

Mas-Marzá, E ;

Segarra, AM ;

Claver, C ;

Peris, E ;

Fernandez, E .

TETRAHEDRON LETTERS, 2003, 44 (35) :6595-6599

← 1 2 →