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- Heck–Matsuda_reaction abstract "The Heck-Matsuda (HM) reaction is an organic reaction and a type of palladium catalysed arylation of olefins that uses arenediazonium salts as an alternative to aryl halides and triflates.The use of arenediazonium salts presents some advantages over traditional aryl halide electrophiles, for example, the use of phosphines as ligand are not required and thus negating the requirement for anaerobic conditions, which makes the reaction more practical and easier to handle. Additionally, the reaction can be performed with or without a base and is often faster than traditional Heck protocols.Allylic alcohols, conjugated alkenes, unsaturated heterocycles and unactivated alkenes are capable of being arylated with arenediazonium salts using simple catalysts such as palladium acetate (Pd(OAc)2) or tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) at room temperature in air, and in benign and conventional solvents.In addition to the intermolecular variant of the HM reaction, intramolecular cyclization processes have also been developed for the construction of a range of oxygen and nitrogen heterocycles.The catalytic cycle for the Heck-Matsuda arylation reaction has four main steps: oxidative addition, migratory insertion or carbopalladation, syn β-elimination and reductive elimination. The proposed Heck catalytic cycle involving cationic palladium with diazonium salts was reinforced by studies with mass spectrometry (ESI) by Correia and co-workers. These results also show the complex interactions that occur in the coordination sphere of palladium during the Heck reaction with arenediazonium salt.".
- Heck–Matsuda_reaction thumbnail HM_faster_than_Heck.gif?width=300.
- Heck–Matsuda_reaction wikiPageID "31041801".
- Heck–Matsuda_reaction wikiPageLength "3907".
- Heck–Matsuda_reaction wikiPageOutDegree "34".
- Heck–Matsuda_reaction wikiPageRevisionID "596614073".
- Heck–Matsuda_reaction wikiPageWikiLink Alkene.
- Heck–Matsuda_reaction wikiPageWikiLink Allyl_alcohol.
- Heck–Matsuda_reaction wikiPageWikiLink Aryl.
- Heck–Matsuda_reaction wikiPageWikiLink Aryl_halide.
- Heck–Matsuda_reaction wikiPageWikiLink Carbopalladation.
- Heck–Matsuda_reaction wikiPageWikiLink Catalysis.
- Heck–Matsuda_reaction wikiPageWikiLink Catalytic_cycle.
- Heck–Matsuda_reaction wikiPageWikiLink Category:Name_reactions.
- Heck–Matsuda_reaction wikiPageWikiLink Category:Organic_reactions.
- Heck–Matsuda_reaction wikiPageWikiLink Conjugated_alkene.
- Heck–Matsuda_reaction wikiPageWikiLink Diazonium_compound.
- Heck–Matsuda_reaction wikiPageWikiLink Electrophile.
- Heck–Matsuda_reaction wikiPageWikiLink Heck_reaction.
- Heck–Matsuda_reaction wikiPageWikiLink Heterocyclic_compound.
- Heck–Matsuda_reaction wikiPageWikiLink Intramolecular_cyclization.
- Heck–Matsuda_reaction wikiPageWikiLink Ligand.
- Heck–Matsuda_reaction wikiPageWikiLink Mass_spectrometry.
- Heck–Matsuda_reaction wikiPageWikiLink Migratory_insertion.
- Heck–Matsuda_reaction wikiPageWikiLink Organic_reaction.
- Heck–Matsuda_reaction wikiPageWikiLink Oxidative_addition.
- Heck–Matsuda_reaction wikiPageWikiLink Palladium.
- Heck–Matsuda_reaction wikiPageWikiLink Palladium(II)_acetate.
- Heck–Matsuda_reaction wikiPageWikiLink Palladium-catalyzed_coupling_reactions.
- Heck–Matsuda_reaction wikiPageWikiLink Phosphine.
- Heck–Matsuda_reaction wikiPageWikiLink Reductive_elimination.
- Heck–Matsuda_reaction wikiPageWikiLink Saturation_(chemistry).
- Heck–Matsuda_reaction wikiPageWikiLink Syn_β-elimination.
- Heck–Matsuda_reaction wikiPageWikiLink Trifluoromethanesulfonate.
- Heck–Matsuda_reaction wikiPageWikiLink Tris(dibenzylideneacetone)dipalladium(0).
- Heck–Matsuda_reaction wikiPageWikiLink File:HM_Mechanism.gif.
- Heck–Matsuda_reaction wikiPageWikiLink File:HM_faster_than_Heck.gif.
- Heck–Matsuda_reaction wikiPageWikiLink File:Intramolecular_HM.gif.
- Heck–Matsuda_reaction wikiPageWikiLink File:Olefins_in_HM_reaction.gif.
- Heck–Matsuda_reaction wikiPageWikiLinkText "Heck–Matsuda reaction".
- Heck–Matsuda_reaction wikiPageUsesTemplate Template:Reaction-stub.
- Heck–Matsuda_reaction subject Category:Name_reactions.
- Heck–Matsuda_reaction subject Category:Organic_reactions.
- Heck–Matsuda_reaction hypernym Reaction.
- Heck–Matsuda_reaction type Disease.
- Heck–Matsuda_reaction type Eponym.
- Heck–Matsuda_reaction type Reaction.
- Heck–Matsuda_reaction type Redirect.
- Heck–Matsuda_reaction comment "The Heck-Matsuda (HM) reaction is an organic reaction and a type of palladium catalysed arylation of olefins that uses arenediazonium salts as an alternative to aryl halides and triflates.The use of arenediazonium salts presents some advantages over traditional aryl halide electrophiles, for example, the use of phosphines as ligand are not required and thus negating the requirement for anaerobic conditions, which makes the reaction more practical and easier to handle.".
- Heck–Matsuda_reaction label "Heck–Matsuda reaction".
- Heck–Matsuda_reaction sameAs Q2223372.
- Heck–Matsuda_reaction sameAs Heck-Matsuda-reactie.
- Heck–Matsuda_reaction sameAs m.0gg6tf3.
- Heck–Matsuda_reaction sameAs Q2223372.
- Heck–Matsuda_reaction wasDerivedFrom Heck–Matsuda_reaction?oldid=596614073.
- Heck–Matsuda_reaction depiction HM_faster_than_Heck.gif.
- Heck–Matsuda_reaction isPrimaryTopicOf Heck–Matsuda_reaction.