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- Negishi_coupling abstract "The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon-carbon bonds (c-c) in the process. A palladium (0) species is generally utilized as the metal catalyst, though nickel is sometimes used: The leaving group X is usually chloride, bromide, or iodide, but triflate and acetyloxy groups are feasible as well. X = Cl usually leads to slow reactions. The organic residue R = alkenyl, aryl, allyl, alkynyl or propargyl. The halide X' in the organozinc compound can be chloride, bromine or iodine and the organic residue R1 is alkenyl, aryl, allyl, alkyl benzyl, homoallyl, and homopropargyl. The metal M in the catalyst is nickel or palladium The ligand L in the catalyst can be triphenylphosphine, dppe, BINAP or chiraphosPalladium catalysts in general have higher chemical yields and higher functional group tolerance.The Negishi coupling finds common use in the field of total synthesis as a method for selectively forming c-c bonds between complex synthetic intermediates. The reaction allows for the coupling of sp3, sp2, and sp carbons, (see orbital hybridization) which make it somewhat unique among the Palladium-catalyzed coupling reactions. Organozincs are moisture and air sensitive, so the Negishi coupling must be performed in an oxygen and water free environment, a fact that has hindered its use relative to other cross-coupling reactions that require less robust conditions (i.e. Suzuki reaction). However, organozincs are more reactive than both organostannanes and organoborates which correlates to faster reaction times.The reaction is named after Ei-ichi Negishi who was a co-recipient of the 2010 Nobel Prize in Chemistry for the discovery and development of this reaction.".
- Negishi_coupling thumbnail NegishiScheme1.png?width=300.
- Negishi_coupling wikiPageExternalLink negishi-coupling.shtm.
- Negishi_coupling wikiPageExternalLink negishi-coupling.
- Negishi_coupling wikiPageID "5697044".
- Negishi_coupling wikiPageLength "22384".
- Negishi_coupling wikiPageOutDegree "109".
- Negishi_coupling wikiPageRevisionID "681151197".
- Negishi_coupling wikiPageWikiLink 1,2-Bis(diphenylphosphino)ethane.
- Negishi_coupling wikiPageWikiLink 2,2-Bipyridine.
- Negishi_coupling wikiPageWikiLink 2,2-bipyridine.
- Negishi_coupling wikiPageWikiLink Acetyloxy.
- Negishi_coupling wikiPageWikiLink Air_sensitivity.
- Negishi_coupling wikiPageWikiLink Akira_Suzuki_(chemist).
- Negishi_coupling wikiPageWikiLink Alkaloid.
- Negishi_coupling wikiPageWikiLink Alkaloids.
- Negishi_coupling wikiPageWikiLink Alkene.
- Negishi_coupling wikiPageWikiLink Alkenyl.
- Negishi_coupling wikiPageWikiLink Alkyl.
- Negishi_coupling wikiPageWikiLink Alkyne.
- Negishi_coupling wikiPageWikiLink Alkynyl.
- Negishi_coupling wikiPageWikiLink Allyl.
- Negishi_coupling wikiPageWikiLink Aryl.
- Negishi_coupling wikiPageWikiLink Asthma.
- Negishi_coupling wikiPageWikiLink BINAP.
- Negishi_coupling wikiPageWikiLink Benzyl.
- Negishi_coupling wikiPageWikiLink Biphenyl.
- Negishi_coupling wikiPageWikiLink Bromide.
- Negishi_coupling wikiPageWikiLink Bromine.
- Negishi_coupling wikiPageWikiLink CPhos.
- Negishi_coupling wikiPageWikiLink Carbon-carbon_bond.
- Negishi_coupling wikiPageWikiLink Carbon–carbon_bond.
- Negishi_coupling wikiPageWikiLink Catalysis.
- Negishi_coupling wikiPageWikiLink Catalyst.
- Negishi_coupling wikiPageWikiLink Category:Carbon-carbon_bond_forming_reactions.
- Negishi_coupling wikiPageWikiLink Category:Condensation_reactions.
- Negishi_coupling wikiPageWikiLink Category:Name_reactions.
- Negishi_coupling wikiPageWikiLink Chemical_synthesis.
- Negishi_coupling wikiPageWikiLink Chemical_yield.
- Negishi_coupling wikiPageWikiLink Chemotherapy.
- Negishi_coupling wikiPageWikiLink Chiraphos.
- Negishi_coupling wikiPageWikiLink Chloride.
- Negishi_coupling wikiPageWikiLink Cis–trans_isomerism.
- Negishi_coupling wikiPageWikiLink Concerted_reaction.
- Negishi_coupling wikiPageWikiLink Coupling_reaction.
- Negishi_coupling wikiPageWikiLink Cross-coupling_reaction.
- Negishi_coupling wikiPageWikiLink Cytotoxicity.
- Negishi_coupling wikiPageWikiLink DNA_polymerase.
- Negishi_coupling wikiPageWikiLink Dehalogenation.
- Negishi_coupling wikiPageWikiLink Dppe.
- Negishi_coupling wikiPageWikiLink Ei-ichi_Negishi.
- Negishi_coupling wikiPageWikiLink Ester.
- Negishi_coupling wikiPageWikiLink Ferrocene.
- Negishi_coupling wikiPageWikiLink Folk_medicine.
- Negishi_coupling wikiPageWikiLink Functional_group.
- Negishi_coupling wikiPageWikiLink Grignard_reaction.
- Negishi_coupling wikiPageWikiLink Grignard_reagens.
- Negishi_coupling wikiPageWikiLink Halocarbon.
- Negishi_coupling wikiPageWikiLink Halogenation.
- Negishi_coupling wikiPageWikiLink Haloketone.
- Negishi_coupling wikiPageWikiLink Heck_reaction.
- Negishi_coupling wikiPageWikiLink Hexaferrocenylbenzene.
- Negishi_coupling wikiPageWikiLink Iodide.
- Negishi_coupling wikiPageWikiLink Iodine.
- Negishi_coupling wikiPageWikiLink Ligand.
- Negishi_coupling wikiPageWikiLink Natural_product.
- Negishi_coupling wikiPageWikiLink Nickel.
- Negishi_coupling wikiPageWikiLink Nobel_Prize_in_Chemistry.
- Negishi_coupling wikiPageWikiLink Novartis.
- Negishi_coupling wikiPageWikiLink Orbital_hybridisation.
- Negishi_coupling wikiPageWikiLink Orbital_hybridization.
- Negishi_coupling wikiPageWikiLink Organoaluminium_chemistry.
- Negishi_coupling wikiPageWikiLink Organoaluminum_chemistry.
- Negishi_coupling wikiPageWikiLink Organotin_chemistry.
- Negishi_coupling wikiPageWikiLink Organotin_compound.
- Negishi_coupling wikiPageWikiLink Organozinc_compound.
- Negishi_coupling wikiPageWikiLink Oxidative_addition.
- Negishi_coupling wikiPageWikiLink Oxygen.
- Negishi_coupling wikiPageWikiLink Palladium.
- Negishi_coupling wikiPageWikiLink Palladium-catalyzed_coupling_reactions.
- Negishi_coupling wikiPageWikiLink Phosphodiesterase.
- Negishi_coupling wikiPageWikiLink Propargyl.
- Negishi_coupling wikiPageWikiLink Pumiliotoxin.
- Negishi_coupling wikiPageWikiLink Rate_limiting.
- Negishi_coupling wikiPageWikiLink Reductive_elimination.
- Negishi_coupling wikiPageWikiLink Richard_F._Heck.
- Negishi_coupling wikiPageWikiLink SN2_reaction.
- Negishi_coupling wikiPageWikiLink Side_reaction.
- Negishi_coupling wikiPageWikiLink Sn2.
- Negishi_coupling wikiPageWikiLink Sodium_channel.
- Negishi_coupling wikiPageWikiLink Sodium_channels.
- Negishi_coupling wikiPageWikiLink Stereospecificity.
- Negishi_coupling wikiPageWikiLink Stereospecifity.
- Negishi_coupling wikiPageWikiLink Stille_coupling.
- Negishi_coupling wikiPageWikiLink Stille_reaction.
- Negishi_coupling wikiPageWikiLink Suzuki_reaction.
- Negishi_coupling wikiPageWikiLink Synthetic_chemistry.
- Negishi_coupling wikiPageWikiLink Tetrahydrofuran.
- Negishi_coupling wikiPageWikiLink Tetrakis(triphenylphosphine)palladium(0).
- Negishi_coupling wikiPageWikiLink Tin.