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Sonogashira Coupling (sonogashira + coupling)

Distribution by Scientific Domains

Chemistry	100%

Distribution within Chemistry

Organic Chemistry	72%
General & Introductory Chemistry	15%

Terms modified by Sonogashira Coupling

sonogashira coupling reaction

Selected Abstracts

Fluoride-Free Hiyama and Copper- and Amine-Free Sonogashira Coupling in Air in a Mixed Aqueous Medium by a Series of PEPPSI-Themed Precatalysts,

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, Issue 12 2009
Chandrakanta Dash
Abstract A new series of robust, user-friendly, and highly active PEPPSI-themed (pyridine-enhanced precatalyst preparation, stabilization and initiation) (NHC)PdX2(pyridine)-type (X = Cl, Br) precatalysts of C4,C5 saturated imidazole- (1,4) and triazole-based (5 and 6) N-heterocyclic carbenes for the Hiyama and Sonogashira couplings under amenable conditions are reported. Specifically 1,6 efficiently catalyze the fluoride-free Hiyama coupling of aryl halides with PhSi(OMe)3 and CH2=CHSi(OMe)3 in air in the presence of NaOH as a base in a mixed aqueous medium (dioxane/H2O, 2:1 v/v). Along the same lines, these 1,6 precatalysts also promote the Cu-free and amine-free Sonogashira coupling of aryl bromides and iodides with phenylacetylene in air and in a mixed aqueous medium (DMF/H2O, 3/1 v/v). The complexes 1,6 were synthesized by the direct reaction of the respective imidazolinium and triazolium halide salts with PdCl2 in pyridine in the presence of K2CO3 as a base. DFT studies on the catalytically relevant palladium(0) (NHC)Pd(pyridine) precursors 1a,6a reveal significant donation from the N-heterocyclic carbene lone pair onto the unfilled ,* orbital of the trans Pd,pyridine bond. This weakens the Pd-bound "throwaway" pyridine ligand, and its dissociation marks the initiation of the catalytic cycle.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) [source]

Conventional Tetrakis(triphenylphosphine)palladium-Copper(I) Iodide-Catalyzed Sonogashira Coupling of Free and BOC- Protected Propargylic Amines "On Water"

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 11-12 2009
Bartomeu Soberats
Abstract Alkynylation of aryl iodides with propargylic amines has been achieved by means of a Sonogashira coupling using "on water" methods. The use of less than 0.2,mol% of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] and 1.5,mol% copper(I) iodide [CuI] in the presence of diisopropylethylamine (DIPEA) allows the coupling to proceed at 95,°C yielding moderate to good yields of mono-, bis-, and tris-aminoalkynylbenzene derivatives. [source]

A Convenient High Activity Catalyst for the Sonogashira Coupling of Aryl Bromides

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 9 2005
Axel Köllhofer
Abstract A mixture of Na2PdCl4, CuI and (t -Bu)3PH+BF4, (molar ratio 4,:,3,:,8) dispersed in H2N(i -Pr)2+Br, can be used as a "single source" precatalyst for the Sonogashira coupling of aryl bromides with various aryl- and alkylacetylenes in HN(i -Pr)2 solvent. Arylacetylenes require just 0.005,mol,% of Pd catalyst at 80,°C, with TOFs ranging between 3,200 and 10,000,h,1. [source]

ChemInform Abstract: Unexpected Domino Reaction via Pd-Catalyzed Sonogashira Coupling of Benzimidoyl Chlorides with 1,6-Enynes and Cyclization to Synthesize Quinoline Derivatives.

CHEMINFORM, Issue 24 2010
Guo-Lin Gao
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Conventional Tetrakis(triphenylphosphine)palladium-Copper(I) Iodide-Catalyzed Sonogashira Coupling of Free and BOC-Protected Propargylic Amines "On Water".

CHEMINFORM, Issue 1 2010
Bartomeu Soberats
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Consecutive Three-Component Synthesis of Ynones by Decarbonylative Sonogashira Coupling

CHEMINFORM, Issue 38 2009
Eugen Merkul
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Simple Indole Synthesis by One-Pot Sonogashira Coupling,NaOH-Mediated Cyclization.

CHEMINFORM, Issue 15 2009
Roberto Sanz
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Copper-Free Sonogashira Coupling in Amine,Water Solvent Mixtures.

CHEMINFORM, Issue 13 2009
Anna Komaromi
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Development of a One-Pot Sequential Sonogashira Coupling for the Synthesis of Benzofurans.

CHEMINFORM, Issue 51 2008
Marton Csekei
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Rapid and Efficient Pd-Catalyzed Sonogashira Coupling of Aryl Chlorides.

CHEMINFORM, Issue 50 2008
He Huang
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

ChemInform Abstract: Copper-Free Sonogashira Coupling of Acid Chlorides with Terminal Alkynes in the Presence of a Reusable Catalyst: An Improved Synthesis of 3-Iodochromenones (= 3-Iodo-4H-1-benzopyran-4-ones).

CHEMINFORM, Issue 26 2008
Pravin R. Likhar
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a "Full Text" option. The original article is trackable via the "References" option. [source]

Facile Synthesis of Substituted Thiophenes via Pd/C-Mediated Sonogashira Coupling in Water.

CHEMINFORM, Issue 11 2007
Sirisilla Raju
Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source]

Regioselective Synthesis of 6-Benzylthiazolo[3,2-b]1,2,4-triazoles During Sonogashira Coupling.

CHEMINFORM, Issue 26 2005
Majid M. Heravi
Abstract For Abstract see ChemInform Abstract in Full Text. [source]

Aqueous Ammonia as a New Activator for Sonogashira Coupling.

CHEMINFORM, Issue 21 2005
Mohamed S. Mohamed Ahmed
Abstract For Abstract see ChemInform Abstract in Full Text. [source]

Sonogashira Coupling with Aqueous Ammonia Directed to the Synthesis of Azotolane Derivatives.

CHEMINFORM, Issue 4 2005
Mohamed S. Mohamed Ahmed
Abstract For Abstract see ChemInform Abstract in Full Text. [source]

New Entry to a Three-Component Pyrimidine Synthesis by TMS,Ynones via Sonogashira Coupling.

CHEMINFORM, Issue 4 2004
Alexei S. Karpov
Abstract For Abstract see ChemInform Abstract in Full Text. [source]

Total Synthesis of a Biotinylated Derivative of Phorboxazole A via Sonogashira Coupling.

CHEMINFORM, Issue 43 2003
T. Matthew Hansen
No abstract is available for this article. [source]

Facile One-Pot Coupling,Aminovinylation Approach to Push,Pull Chromophores: Alkyne Activation by Sonogashira Coupling.

CHEMINFORM, Issue 26 2003
Alexei S. Karpov
Abstract For Abstract see ChemInform Abstract in Full Text. [source]

Fluoride-Free Hiyama and Copper- and Amine-Free Sonogashira Coupling in Air in a Mixed Aqueous Medium by a Series of PEPPSI-Themed Precatalysts,

Systematic Studies on Photoluminescence of Oligo(arylene-ethynylene)s: Tunability of Excited States and Derivatization as Luminescent Labeling Probes for Proteins

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 14 2006
Yong-Gang Zhi
Abstract Functionalized oligo(phenylene-ethynylene)s (OPEs) with different conjugation lengths, p -X(C6H4C,C)nSiMe3 (n = 1,4; X = NH2, NMe2, H) were synthesized by Sonogashira coupling of (phenylene-ethynylene)s and 1-iodo-4-(trimethylsilylethynyl)benzene, followed by desilylation of the p -substituted (trimethylsilylethynyl)benzenes with potassium hydroxide. The photoluminescent properties for the OPE series with different chain lengths and their solvatochromic responses were examined. The absorption maxima were red-shifted with increasing numbers of ,(C6H4C,C), units (n), and a linear plot of the absorption energy maxima vs. 1/n was obtained for each series. The emission spectra in dichloromethane showed a broad and structureless band, the energies of which (in wavenumbers) also fit linearly with 1/n. Both the absorption and emission wavelength maxima of the NH2 - and NMe2 -substituted OPEs exhibited significant solvent dependence, whereas the parent OPEs (X = H) showed only minor shifts of the ,max values in different solvents. Substituent effects upon the photoluminescent characteristics of the OPEs and the tunability of the excited states were examined with the p -X(C6H4C,C)nSiMe3 (n = 2, 3; X = NH2, NMe2, H, SMe, OMe, OH, and F) series. The H- and F-substituted counterparts exhibited high-energy vibronically structured emissions attributed to the 3(,,*) excited states of the (arylene-ethynylene) backbone. For compounds bearing NH2 and NMe2 groups, a broad red-shifted emission with a remarkable Stokes shift from the respective absorption maximum was observed, which can be assigned to an n , ,* transition. The n , ,* assignment was supported by MO calculations on the model compounds p -X(C6H4C,C)2SiH3 (X = NH2, H). Functionalization of the oligo(arylene-ethynylene)s with the N -hydroxysuccinimidyl (NHS) moiety enabled covalent attachment of the fluorophore to HSA protein molecules. A series of fluorescent labels, namely p -X(C6H4C,C)nC6H4NHS, (n = 1, X = NH2, NMe2, SMe, OMe, OH, F; n = 2, X = NH2, NMe2) and p -Me2NC6H4C,C(C4H2S)C,CC6H4NHS were synthesized, and their conjugates with HSA (human serum albumin) were characterized by MALDI-TOF mass spectrometry, UV/Vis absorption spectroscopy, and gel electrophoresis. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006) [source]

Oligonucleotide Analogues with Integrated Bases and Backbone.

HELVETICA CHIMICA ACTA, Issue 12 2006

Abstract The self-complementary UA and AU dinucleotide analogues 41,45, 47, 48, and 51,60 were prepared by Sonogashira coupling of 6-iodouridines with C(5,) -ethynylated adenosines and of 8-iodoadenosines with C(5,) -ethynylated uridines. The dinucleotide analogues associate in CDCl3 solution. The C(6/I) -unsubstituted AU dimers 51 and 54 prefer an anti -oriented uracilyl group and form stretched linear duplexes. The UA propargyl alcohols 41 and 43,45 possess a persistent intramolecular O(5,/I)H,,,N(3/I) H-bond and, thus, a syn -oriented adeninyl and a gt - or tg -oriented ethynyl moiety; they form corrugated linear duplexes. All other dimers form cyclic duplexes characterized by syn -oriented nucleobases. The preferred orientation of the ethynyl moiety (the C(4,),C(5,) torsion angle) defines a conformation between gg and one where the ethynyl group eclipses O(4,/I). The UA dimers 42, 47, and 48 form Watson,Crick H-bonds, the AU dimers 56 and 58,60 H-bonds of the Watson,Crick -type, the AU dimers 53 and 55 reverse- Hoogsteen, and 57Hoogsteen H-bonds. The pairing mode depends on the substituent of C(5,/I) (H, OSiiPr3; OH) and on the H-bonds of HOC(5,/I) in the AU dimers. Association constants were derived from the concentration-dependent chemical shift for HN(3) of the uracilyl moiety; they vary from 45,104,M,1 for linear duplexes to 197,2307,M,1 for cyclic duplexes. The thermodynamic parameters were determined by van't Hoff analysis of the temperature-dependence of the (concentration-dependent) chemical shift for HN(3) of the uracilyl moiety. Neglecting stacking energies, one finds an average energy of 3.5,4.0,kcal/mol per intermolecular H-bond. Base stacking is evidenced by the temperature-dependent CD spectra. The crystal structure of 54 shows two antiparallel chains of dimers connected by Watson-Crick H-bonds. The chains are bridged by a strong H-bond between the propargylic OH and OC(4) and by weak reverse A,,,A Hoogsteen H-bonds. [source]

A Novel Coupling 1,3-Dipolar Cycloaddition Sequence as a Three-Component Approach to Highly Fluorescent Indolizines

HELVETICA CHIMICA ACTA, Issue 7 2005
Alexandru
Indolizines 4 and biindolizines 6 can be synthesized in moderate yields in a consecutive one-pot three-component process by a coupling/1,3-dipolar cycloaddition sequence of a (hetero)arenecarbonyl chloride 1, a terminal alkyne 2, and a suitable 1-(2-oxoethyl) pyridinium bromide 3 or 5, respectively (Schemes,1 and 2). After the Sonogashira coupling, a [2+3] cycloaddition of the in situ formed pyridinium ylide, an allyl-type 1,3-dipole, furnishes a cycloadduct that is instantaneously oxidatively aromatized to give the highly fluorescent indolizine derivatives that were unambiguously characterized by an X-ray-structure analysis of compound 4d (Fig.,1). Additionally, fluorescence studies with pyridinyl-substituted representatives reveal not only that indolizines and biindolizines are highly interesting fluorescence dyes but that their fluorescence color can also be reversibly switched upon altering the pH of the medium. [source]

Palladium-Catalyzed Sequential Reactions via Allene Intermediates for the Rapid Synthesis of Fused Polycyclic Pyrrole Derivatives

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 18 2009
Xian Huang
Abstract In this paper, we report a novel sequential reaction sequence consisting of a series of processes including Sonogashira coupling, propargyl-allenyl isomerization, [3+2],cycloaddition, denitrogenation, and highly selective biradical coupling reaction, providing an efficient synthesis of fused polycyclic pyrrole derivatives. The reaction features one CC bond and two CN bonds formed to construct the pyrrole unit, together with two rings efficiently assembled in one stroke. [source]

Facile Synthesis of Polycyclic Fluorene Derivatives via a Palladium-Catalyzed Coupling, Propargyl-Allenyl Isomerization and Schmittel Cyclization Sequence

ADVANCED SYNTHESIS & CATALYSIS (PREVIOUSLY: JOURNAL FUER PRAKTISCHE CHEMIE), Issue 17 2009
Ruwei Shen
Abstract A stepwise process involving Sonogashira coupling, propargyl-allenyl isomerization and Schmittel cyclization has been realized, leading to an efficient synthesis of polycyclic fluorene derivatives from readily available starting materials. The reaction features the formation of three new carbon-carbon bonds to construct the benzene unit together with an efficient assembly of three or four rings in a single operative step. [source]

Conventional Tetrakis(triphenylphosphine)palladium-Copper(I) Iodide-Catalyzed Sonogashira Coupling of Free and BOC- Protected Propargylic Amines "On Water"

A Convenient High Activity Catalyst for the Sonogashira Coupling of Aryl Bromides

New calcineurin inhibiting 3-dimethylaminopropyl substituted diarylheterocycles by sonogashira reactions and catalytic hydrogenation

JOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 7 2005
Lunxiang Yin
A series of calcineurin inhibiting compounds 1 consisting of a central aromatic N-heterocycle, two aryl substituents and a 3-dimethylaminopropyl chain was synthesized by introduction of the side chain. A corresponding haloheterocycle 3 was transformed into a 3-dimethylaminopropynylheterocycle 2 by Sonogashira coupling and was in turn hydrogenated in the presence of Pd/C to afford the 3-dimethylaminopropyl-sub-stiuted heterocycles 1. Some of the products showed calcineurin inhibiting activity. [source]

A New Efficient Route to Chiral 1,3-Disubstituted Ferrocenes: Application to the Syntheses of (Rp)- and (Sp)-17,-[(3,-formylferrocenyl)ethynyl]estradiol

CHEMISTRY - A EUROPEAN JOURNAL, Issue 7 2006
Benoît Ferber
Abstract Starting from (2S,4S)-2-ferrocenyl-4-(methoxymethyl)-1,3-dioxane (4), use of the stereogenic ortho -directing menthyl para- tolyl sulfoxide group, which occupies the 2, position in the ferrocenyl ring and redirects subsequent lithiation to the 3, position, allowed the synthesis of optically pure (Sp)-1-formyl-3-iodoferrocene (8), that was characterized by single-crystal X-ray diffraction. Combination of this method with a protection,deprotection strategy, using trimethylsilyl as a temporary blocking group, yielded (Rp)-1-formyl-3-iodoferrocene (13). Separate Sonogashira coupling of each of the enantiomeric iodoformylferrocenes 8 and 13 with 17,-ethynyl-estradiol produced (Rp)-17,-[(3,-formylferrocenyl)ethynyl]estradiol (14) and (Sp)-17,-[(3,-formylferrocenyl)ethynyl]estradiol (15), respectively. [source]

Highly Potent Naphthofuran-Based Retinoic Acid Receptor Agonists

CHEMMEDCHEM, Issue 5 2009
Efrén, Pérez Santín Dr.
Abstract A series of arotinoids with a central benzofuran or naphthofuran ring structure were synthesized by an efficient three-step process. Most of these 3-substituted naphthofuran arotinoids are potent agonists of the retinoic acid receptor (RAR) subtypes, with activities in the nanomolar range. A collection of arotinoids with a central benzofuran or naphthofuran ring structure was efficiently synthesized by a three-step process that comprises a Sonogashira coupling, an iodine-induced 5- endo -dig cyclization of the o -methoxyphenyl- or naphthyl-ethynyl benzoates, and finally a Suzuki/Sonogashira coupling of the corresponding 3-iodobenzo- or naphthofurans. Most of these 3-substituted naphthofuran arotinoids (but not the 5,7-di- tert -butylbenzofurans with the same substitution pattern at the C2 and C3 positions) are potent agonists of the retinoic acid receptor (RAR) subtypes, with activities in the nanomolar range. [source]