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Sonogashira Cross-coupling Reaction (sonogashira + cross-coupling_reaction)

Distribution by Scientific Domains

Chemistry	90%

Selected Abstracts

Configurational Isomers of a Stilbene-Linked Bis(porphyrin) Tweezer: Synthesis and Fullerene-Binding Studies

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 35 2009
Maher Fathalla
Abstract A new stilbene-tethered bis(porphyrin) tweezer 5 has been synthesized through a Sonogashira cross-coupling reaction. The tweezer exists as two configurational isomers [(Z) + (E)], which have distinct cavity sizes. Fullerene-binding studies show that the (Z) isomer of the tweezer has a significantly higher affinity toward both C60 and C70 compared to the (E) congener. In addition, the (Z) , (E) photoisomerization of tweezer 5 is also discussed. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) [source]

Synthesis and Photophysical Properties of a Pyrazolino[60]fullerene with Dimethylaniline Connected by an Acetylene Linkage

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 10 2006
Andreas Gouloumis
Abstract A new triad based on pyrazolino[60]fullerene and a conjugated dimethylaniline group has been synthesized by a copper-free Sonogashira cross-coupling reaction using microwave irradiation as the source of energy. The electrochemical and photophysical properties of the triad were systematically investigated by techniques such as time-resolved fluorescence and transient absorption spectroscopy. Charge separation via the excited singlet state of the C60 moiety was confirmed in polar and nonpolar solvents and competes with triplet formation of the C60 moiety. The charge-separated state persisted for 91 ns. Such long lifetimes are characteristic of long distances between the radical anion of the pyrazolino[60]fullerene derivative and the radical cation of the dimethylaniline moiety. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006) [source]

Synthesis of 4-[18F]fluoroiodobenzene and its application in sonogashira cross-coupling reactions

JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, Issue 8 2003
Frank R. Wüst
Abstract The first application of a Sonogashira cross-coupling reaction in 18F chemistry has been developed. The reaction was exemplified by the cross-coupling of terminal alkynes (ethynylcyclopentyl carbinol 6, 17,-ethynyl-3,17,-estradiol 7 and 17,-ethynyl-3-methoxy-3,17,-estradiol 8) with 4-[18F]fluoroiodobenzene. 4,4,-Diiododiaryliodonium salts were used as precursors for the synthesis of 4-[18F]fluoroiodobenzene, enabling the convenient access to 4-[18F]fluoroiodobenzene in 13,70% yield using conventional heating or microwave activation. The Sonogashira cross-coupling of 4-[18F]fluoroiodobenzene with terminal alkynes gave the corresponding 4-[18F]fluorophenylethynyl-substituted compounds [18F]-9, [18F]-10 and [18F]-13 in yields up to 88% within 20 min of starting from 4-[18F]fluoroiodobenzene. Copyright © 2003 John Wiley & Sons, Ltd. [source]

Synthesis of Furo[2,3- b]pyrazine Nucleoside Analogues with 1,2,3-Triazole Linkage

MOLECULAR INFORMATICS, Issue 11-12 2007
Denis
Abstract Sonogashira coupling reaction with the readily available 1-(4-methoxybenzyl)-3,5-dichloropyrazin-2(1H)-ones was followed by mild silver-catalyzed cyclization to provide the corresponding 2-chlorofuro[2,3- b]pyrazines in excellent yields. A second Sonogashira cross-coupling reaction resulted in the formation of 2-ethynylfuro[2,3- b]pyrazines, which were coupled with D -ribose and 2-deoxy- D -ribose using a microwave-assisted Cu(I)-catalyzed Huisgen [2+3] dipolar cycloaddition reaction, to generate a small library of new nucleoside analogues. [source]

An improved practical Pd/C-catalyzed Sonogashira cross-coupling reaction for the synthesis of liquid crystals of trans-cyclohexyltolans

APPLIED ORGANOMETALLIC CHEMISTRY, Issue 6 2010
Hongyong Shang
Abstract An improved practical synthesis of liquid crystals of trans-cyclohexyltolans by Sonogashira cross-coupling reaction of 1-iodo-4-(trans-4-alkylcyclohexyl)benzene with aromatic terminal alkynes in the presence of Pd/C (palladium on activated carbon) as low as 0.03 mol% of Pd and CuI (2 mol%) in a mixture solvent of acetone,water (5:2 in volume) is described. The liquid crystals could be obtained in high yields as a solid with excellent purity by simple filtration, and the filtrate could be reused several times while still retaining high catalytic activity. Copyright © 2010 John Wiley & Sons, Ltd. [source]

DNA Containing Side Chains with Terminal Triple Bonds: Base-Pair Stability and Functionalization of Alkynylated Pyrimidines and 7-Deazapurines

CHEMISTRY & BIODIVERSITY, Issue 5 2006
Frank Seela
Abstract The synthesis of a series of oligonucleotides containing 5-substituted pyrimidines as well as 7-substituted 7-deazapurines bearing diyne groups with terminal triple bonds is reported. The modified nucleosides were prepared from the corresponding iodo nucleosides and diynes by the Sonogashira cross-coupling reaction. They were converted into phosphoramidites and employed in solid-phase synthesis of oligonucleotides. The effect of the diyne modifications on the duplex stability was investigated. The modified nucleosides were used for further functionalization using the protocol of Huisgen,Sharpless [2+3] cycloaddition (,click chemistry'). [source]

Selective Tuning of the HOMO,LUMO Gap of Carbazole-Based Donor,Acceptor,Donor Compounds toward Different Emission Colors

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 9 2010
Huaqiang Zhang
Abstract Carbazole-based donor,acceptor compounds with tunable HOMO,LUMO gaps were synthesized by Suzuki and Sonogashira cross-coupling reactions. Their optical and electrochemical properties were fully characterized. The results show that materials with different emission colors ranging from blue to green to orange could be obtained. The experimental results were also supported by theoretical calculations. [source]

First Asymmetric Total Synthesis of Penarolide Sulfate A1

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 36 2008
Debendra K. Mohapatra
Abstract Penarolide sulfate A1, with three contiguous stereogenic centers on a macrocyclic skeleton, affords promise as an ,-glucosidase inhibitor. Herein, we describe the first asymmetric total synthesis of this natural product. A stereoselective strategy for rapid assembly of the complete framework of the 30-membered macrocyclic core is delineated herein. Sequential amidation and intramolecular Sonogashira cross-coupling reactions were pivotal to the success of our efforts. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) [source]

Synthesis of hyperbranched polymers with precise conjugation length

JOURNAL OF POLYMER SCIENCE (IN TWO SECTIONS), Issue 6 2007
Jing Li
Abstract A set of AB2 type monodisperse conjugated oligomers carrying two bromo functional groups and one boronic ester functional group were prepared by iterative deprotection and Sonogashira cross-coupling reactions. Suzuki polycondensation of these AB2 type monodisperse oligomers afforded hyperbranched polymers. The hyperbranched conjugated polymers we prepared possess not only precisely controlled conjugation length like monodisperse conjugated oligomers but also the structural feature of hyperbranched polymers. Optical property investigation demonstrated that the maximum absorption and emission wavelength red-shifted along with the increasing of the conjugation length between the two branching points and the hyperbranched structure could effectively reduce the aggregation of the conjugated polymer chains. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 1084,1092, 2007 [source]