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Topic: Sonogashira coupling

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	Coupling reaction - Wikipedia, the free encyclopedia
		A coupling reaction or oxidative coupling in organic chemistry is a catch-all for a range of reactions in Organometallic chemistry where two hydrocarbon radicals are coupled with the aid of a metal containing catalyst.
		the Negishi coupling is a coupling between aryl or vinyl halides with organozinc compounds catalyzed by nickel or palladium
		the Buchwald-Hartwig reaction is a coupling reaction of aryl halides and amines catalyzed by palladium
	en.wikipedia.org /wiki/Coupling_reaction (657 words)

	Frontier Scientific (Site not responding. Last check: 2007-09-19)
		Kumada coupling is a well-established method for forming carbon-carbon bonds with a Grignard reagent and a aryl, vinyl, or alkyl halide.
		When most cross coupling reactions are performed under a CO atmosphere, the reaction produces a ketone by incorporation of CO. Carbonylative coupling is general nomenclature referring to this type of reaction.
		In this reaction an alkyne is coupled to an aromatic halide.
	www.frontiersci.com /refs.htm (512 words)

	Palladium-Catalyzed Coupling of Aryl Halides and
		The Sonogashira coupling is well-known as the synthesis of substituted acetylenes by coupling aryl or vinyl halides with terminal acetylenes in the presence of a palladium catalyst and CuI as cocatalyst.
		Numerous reports describe the coupling of trimethylsilylacetylene with aryl halides in Sonogashira type reactions, and the trimethylsilyl (TMS) group is generally unaffected and thus functions as a protecting group which can be subsequently removed to furnish a new terminal alkyne.
		to explain the palladium-catalyzed coupling of alkenyl-silanes with aryl- and vinylhalides in the presence of tetrabutylammonium fluoride.
	www.mdpi.org /ecsoc/ecsoc-5/Papers/e0019/e0019.htm (872 words)

	Frontier Scientific (Site not responding. Last check: 2007-09-19)
		Sonogashira coupling of functionalized trifloyl oxazoles and thiazoles with terminal alkynes: Synthesis of disubstituted heterocycles.
		Sonogashira coupling and cyclization reactions on alumina: a route to aryl alkynes, 2-substituted-benzoÝb¨furans and 2-substituted-indoles
		Synthesis of 1-aryl-1,3-diyne and 2-aryl-1,1-dialkynylethene from the Sonogashira reactions of 2-aryl-1,1-dibromoethene
	www.frontiersci.com /sonogashirarefs.htm (1563 words)

	Microwave Chemistry Highlights: Hiyama Couplings, Sonogashira/Heteroannulation, β-Glycosylamine Synthesis, ...
		Somewhat related to the well-known Suzuki cross-coupling reaction involving organoboron reagents, is the so-called Hiyama coupling of organosilanes with halides and triflates to form unsymmetrical biaryl compounds.
		Seganish and DeShong from the University of Maryland have described rapid, microwave-promoted Hiyama couplings of bis(catechol) silicates with aryl bromides (Org.
		The reaction could either be performed in a two-step protocol, by first performing a classical Sonogashira coupling on 2-amino-3-chloropyrazine, followed by base-induced cyclization (reaction a), or in a one-step method by reacting the corresponding sulfonamide, N-(3-chloropyrazin-2-yl)-methanesulfonamide, directly with terminal acetylenes in the presence of suitable palladium catalyst (3 mol%) (reaction b).
	www.organic-chemistry.org /Highlights/2004/15December.shtm (557 words)

	OhioLINK ETD: Weisner, Andrew
		Sonogashira Coupling Routes to ortho-Alkynyl- and Fused-Ring Sydnones.
		From this intermediate, several ortho-alkynyl sydnones were prepared via a one-pot desilylation with tetrabutylammonium fluoride and Sonogashira coupling with para-substituted aryl iodides.
		Sonogashira coupling routes were used to add additional para-alkynylphenyl moieties to the above-mentioned ortho-alkynyl sydnones and generate oligomeric alkynyl sydnones.
	www.ohiolink.edu /etd/view.cgi?acc_num=wright1054924552 (377 words)

	ECSOC-5 Poster E0022 Fifth International Electronic Conference on Synthetic Organic Chemistry
		Sonogashira coupling of iodoanilines: Evidence for the absence of non-thermal effects during microwave heating
		When microwave heating is applied the reaction conditions are in many aspects different (high pressure, super heating, hot-spots in case of multimode reactors) from conventional conditions and the reactions applying conventional respective microwave heating are therefore rarely comparable.
		The Sonogashira coupling of iodoanilines was achieved in excellent yields within considerably shorter time than earlier published in the literature.
	www.mdpi.org /ecsoc/ecsoc-5/Papers/e0022/e0022.htm (660 words)

	Amir Faraji - UF Journal of Undergraduate Research Paper
		Proposed mechanism for the palladium mediated coupling of a terminal acetylene with an aryl halide, as applicable to platinum-acetylide polymer and oligomer synthesis.
		Therefore, when a coupling reaction of the type shown in Figure 3 is kinetically difficult to achieve, it is best to use aryliodides.
		First, the coupling of the chromophore with the adamantane must proceed, followed by the coupling of iodobenzene with the terminal acetylene.
	www.clas.ufl.edu /jur/200601/papers/paper_faraji.html (3104 words)

	Recent Journal Articles: Organic Chemistry -- Neurotransmitter.net (via CobWeb/3.1 planetlab2.csres.utexas.edu) (Site not responding. Last check: 2007-09-19)
		Coupled with isotope studies, the reagent shows that the simplest autocatalytic cycle for the consumption of formaldehyde in this process cannot account for the bulk consumption of formaldehyde.
		Palladium/copper-catalyzed Sonogashira cross-coupling reaction of aryl halides with a variety of terminal alkynes under amine-free conditions in dimethylformamide (DMF) at 80 degrees C gave internal arylated alkynes using PdCl2(MeCN)2 with phosphine-free hydrazone 2a as a ligand and CuI as the cocatalyst in good yields.
		By employing the coupling reaction of trans-PtI2(Et3)2 with C-H bonds in alkynes as the key step, two new 60 degrees organometallic subunits with different size from 3,6-dibromophenanthrene were prepared in reasonable yields.
	www.neurotransmitter.net.cob-web.org:8888 /recentorganicchemistry.html (10538 words)

	UDM Faculty Research Page - Faculty Research Highlights
		Of particular note is the family of palladium-catalyzed alkynylation reactions, the Sonogashira cross-coupling being its most prominent member.
		An alliance of the copper-promoted Castro-Stephens reaction and the ethynyl Heck reaction, Sonogashira conditions have proven to be a superior method for alkynylation, especially in the case of arylethynylenes.
		C NMR results established a working model of the operative coupling mechanism: an amidine base- and copper(I)-dependent protodesilylation is responsible for in situ ethynylsilane deprotection.
	www.udmercy.edu /facultyresearch/research.php (1939 words)

	MOTW: Catalytic Platinum and Palladium
		In recent decades a variety of useful coupling reactions that do not require formation of strong nucleophiles have been developed, often exploiting the accessibility of stable organoboron compounds (note 4) and the ease of preparing excellent leaving groups such as triflates (trifluoromethanesulfonate esters) and iodides.
		A sizable number of coupling reactions have been developed, and a great many of these employ palladium in a catalytic role.
		Such reactions include the Suzuki coupling (Figure 4a, coupling of boronic acids or boronate esters and aryl halides/triflates), the Heck reaction (Figure 4b, coupling of aryl or vinyl halides/triflates with α,β-unsaturated carbonyl compounds), and the Sonogashira coupling (Figure 4c, coupling of terminal alkynes with aryl or vinyl halides/triflates).
	www.nitrogenorder.org /molweek/aug2005/07aug05.shtml (1737 words)

	[No title]
		The first report of a coupling reaction resulting in the formation of a carbon-carbon bond formation at C5 was due du F.W. Hobbs (1989) who reported the synthesis of the alkynylamino nucleosides 6 and 8 from the iodo precursors 5 and 7, respectively.
		Thus, coupling of triflate 22 with 4-pentynoic acid in the presence of catalytic amounts of Pd(OAc)2Cl2 and CuI afforded 23 in 89% chemical yield (Scheme 7).
		Hence, it is not surprising that palladium-catalyzed coupling reactions involving this class of compouds have not been much studied.
	www.atlanchim.com /Anglais/scientificletter/ls3/ls3_2.htm (1061 words)

	ISP Fine Chemicals
		The reaction, first reported by Kenkichi Sonogashira and Nobue Hagihara in 1975 is a coupling reaction of terminal alkynes with aryl or vinyl halides.
		It has turned out out to be one of the most important reactions performed in the Industry for C-C Coupling.
		This coupling of terminal alkynes with aryl or vinyl halides is performed with a palladium catalyst, a copper(I) cocatalyst, and an amine base.
	ispcorp.com /products/finechem/content/brochure/Sonogashira/index.html (144 words)

	Tandem sonogashira coupling: an efficient tool for the synthesis of diarylalkynes. (via CobWeb/3.1 ... (Site not responding. Last check: 2007-09-19)
		Several aryl halides were coupled with 2-methyl-3-butyn-2-ol as acetylene source in the presence of PdCl(2)(PPh(3))(2) and CuI.
		Following the deprotection of the acetylene moiety in the same pot using a strong base, the Sonogashira coupling of a second aryl halide led to the formation of the appropriate diarylakyne.
		The primary disadvantage of the coupling methods is the kinetically determined product distribution, since a significant portion of oligomers grow beyond the length of the cyclic targets ("overshooting").
	lib.bioinfo.pl.cob-web.org:8888 /pmid:15606099 (807 words)

	Synthesis of conformationally constrained cyclic peptides using an intramolecular sonogashira coupling. (via CobWeb/3.1 ... (Site not responding. Last check: 2007-09-19)
		Small peptides having a 3-bromobenzyl group at the C-termini and n-alkynoyl group at the N-termini undergo a smooth copper-free intramolecular Sonogashira coupling reaction to afford the corresponding cyclic peptides in moderate yields.
		Hongjian Lu, Chaozhong Li N-Tosyl-3-halo-3-butenylamines underwent efficient Ullmann-type coupling with the catalysis of CuI/N,N'-dimethylethylenediamine to afford 2-alkylideneazetidines, which could be readily converted to the corresponding beta-lactams by oxidation with O(3).
		Tripeptides 3a-c and dipeptide 11 were cyclized via an intramolecular Sonogashira reaction, and the cyclic peptides 4a-c and 15a were obtained in 6-23% yield.
	lib.bioinfo.pl.cob-web.org:8888 /pmid:16268647 (763 words)

	A Coupling-Isomerization Sequence As An Entry To A Novel Three Component One-Pot Synthesis of 1,5-Benzoheteroazepines
		With this powerful tool for the construction of chalcones (1,3-diaryl propenones) in hand and considering the mild reaction conditions for the Sonogashira coupling reaction we have developed novel one-pot pyrazoline [8] and pyrimidine [9] syntheses (Scheme 1).
		In particular, the mild reaction conditions of Sonogashira couplings [10] not only allow the presence of sensitive functional groups without tedious protection and deprotection steps but are also advantageous for base-mediated processes such as cyclocondensations.
		Thus, we have submitted p-iodo nitrobenzene (4a), 4-bromo pyridine (4b), or p-bromo benzonitrile (4c), aryl propynols 5 [11] and 2-heteroatom substituted anilines 6 to the reaction conditions of the Sonogashira coupling in boiling mixture of triethylamine and THF [12].
	pages.unibas.ch /mdpi/ecsoc-4/a0074/a0074.htm (1352 words)

	NRC Research Press: Canadian Journal of Chemistry
		Synthesis of acetylenic ketones by a Pd-catalyzed carbonylative three-component coupling reaction in [bmim]PF Takahide Fukuyama, Ryo Yamaura, and Ilhyong Ryu
		Abstract: A carbonylative three-component coupling reaction of aryl iodides with terminal alkynes catalyzed by PdCl
		, was not suitable for this reaction, since the background Sonogashira coupling reaction, a competing reaction, also proceeded.
	pubs.nrc-cnrc.gc.ca /cgi-bin/rp/rp2_abst_e?cjc_v05-031_83_ns_nf_cjc6-05 (164 words)

	Catalysts for Fine Chemical Synthesis, Volume 3, Metal Catalysed Carbon-Carbon Bond-Forming Reactions, Edited by ... (Site not responding. Last check: 2007-09-19)
		Arylation of ketones, aryl amination and Suzuki-Miyaura cross coupling using a well-defined palladium catalyst bearing an N-heterocyclic carbene ligand
		Nonpolar biphasic catalysis: Suzuki- and Sonogashira coupling reactions
		Cross-coupling reaction of alkyl halides with Grignard reagents in the presence of 1,3-butadiene catalysed by nickel, palladium, or copper
	www.chipsbooks.com /catcem3.htm (651 words)

	[No title]
		Potassium trifluoroborates and organoboranes or boronate esters may be used in place of boronic acids.
		Some pseudohalides (for example triflates) may also be used as coupling partners.
		Sulfides cause problems (why?)¡O 2Oª> "ðH ð ð0“”Þ½h¿ÿ ?ð ÿÿÿ»àã33Ì80º___PPT10ë.èÕÆ`Ô¶îï ðpð\ðð( ð ð\ðr ð\ Sð”fç¿ÿð `}ðÃ ç ð ð ² ð\ Óð`AÁÿÿÿÿÿÿ¿ÀÿÃheck-r3ðÐ÷ ðÃçð¿ ð\ £ð<Dñ¤¿¿Àÿð@ÐÊ ðS¨?The palladium-catalyzed C-C coupling between aryl halides or vinyl halides and activated alkenes in the presence of a base is referred as the "Heck Reaction".
	www.ulm.edu /~junk/examkeys/pp_pd_couplings.ppt (379 words)

	Microreactor chemistry
		Microreactor based Other Non-Carbon-Carbon bond forming coupling reactions
		In Situ Quench (formation of nucleophile in presence of electrophile and subsequent carbon carbon bond
		Coupling by other controlled formation of C-O, C-N, C-S bonds
	www.mrsp.net /Chemistry.htm (124 words)

	IngentaConnect A Silica-Supported Copper(I) Catalyzed Sonogashira Coupling React...
		An immobilization of copper(I) in organic-inorganic hybrid materials catalyzed Sonogashira coupling reaction was developed.
		Terminal alkynes reacted with aryl iodides and aryl bromides in the presence of 3-(2-aminoethylamino)propyl functionalized silica gel immobilized copper(I) catalyst, triphenylphosphine and potassium carbonate in DMF.
		Keywords: Sonogashira coupling reaction; organic-inorganic hybrid material; immobilization of copper(I); heterogeneous catalyst
	www.ingentaconnect.com /content/ben/loc/2006/00000003/00000004/art00007 (167 words)

	[No title]
		?ÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿper(I)-catalyzed cross coupling* of allylic carboxylates with Grignard reagents.
		15) Pd-catalyzed Cross coupling Reactions • Couplings of Aryl Chlorides -Littke, A. F.; Fu, G. Palladium-catalyzed coupling reactions of aryl chlorides.
		• Sonogashira Reaction -Sonogashira, K. Development of Pd-Cu catalyzed cross-coupling of terminal acetylenes with sp2-carbon halides.
	www.udel.edu /chem/fox/chem634/2004Chem634RefWk1.doc (1395 words)

	Rapid Homogeneous-Phase Sonogashira Coupling Reactions Using Controlled Microwave Heating (Site not responding. Last check: 2007-09-19)
		Rapid Homogeneous-Phase Sonogashira Coupling Reactions Using Controlled Microwave Heating
		A microwave-enhanced, rapid and efficient homogeneous-phase version of the Sonogashira reaction is presented.
		It has been applied to the coupling of aryl iodides, bromides, triflates, and aryl chloride, as well as pyridine and thiophene derivatives with trimethylsilylacetylene.
	pubs.acs.org /cgi-bin/jtext?joceah/66/i12/abs/jo0057250 (120 words)

	Sonogashira Coupling of Functionalized Trifloyl Oxazoles and Thiazoles with Terminal Alkynes: Synthesis of ... (Site not responding. Last check: 2007-09-19)
		Department of Chemistry and Center for Streamlined Synthesis, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215
		This paper describes Sonogashira cross-coupling of functionalized 2-, 4-, and 5-trifloyl oxazoles and thiazoles with terminal alkynes.
		This methodology has been extended to 2,4-ditrifloylthiazoles, which results in regioselective cross-coupling at the C2-position of the thiazole.
	pubs.acs.org /cgi-bin/abstract.cgi/orlef7/2002/4/i15/abs/ol026099r.html (129 words)

	4 Palladium
		nucleophiles, the cross coupling of organometallic reagents (such as organotin, organoboron and
		In this experiment, 4-nitrobromobenzene is cross coupled with phenylacetylene to give the mixed
		The product is conveniently purified by vacuum sublimation, a clean and much
	www.ch.ic.ac.uk /local/organic/4_Palladium.html (262 words)

	General Catalysts for the Suzuki-Miyaura and Sonogashira Coupling Reactions of Aryl Chlorides and for the Coupling of ...
		General Catalysts for the Suzuki-Miyaura and Sonogashira Coupling Reactions of Aryl Chlorides and for the Coupling of Challenging Substrate Combinations in Water
		The use of sulfonated biarylphosphine ligands provides highly active, stable and versatile catalyst systems for Suzuki-Miyaura and Sonogashira cross-coupling reactions for aqueous-phase processes.
		alkynes, aryl chlorides, boronic acids, cross-coupling, water, Suzuki coupling, Sonogashira reaction
	www.organic-chemistry.org /abstracts/literature/988.shtm (102 words)

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