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- Ullmann_reaction abstract "The Ullmann reaction or Ullmann coupling is a coupling reaction between aryl halides and copper. The reaction is named after Fritz Ullmann, who derived it from a reaction developed by his wife, Irma Goldberg. A typical example is the coupling of 2 o-chloronitrobenzene reactants to form 2,2'-dinitrobiphenyl with a copper - bronze alloy.The traditional version of the Ullmann reaction requires harsh reaction conditions, and the reaction has a reputation for erratic yields. Since its discovery some improvements and alternative procedures have been introduced.The reaction mechanism of the Ullmann reaction is extensively studied. Electron spin resonance rules out a radical intermediate. The oxidative addition / reductive elimination sequence observed with palladium catalysts is unlikely for copper because copper(III) is rarely observed. The reaction probably involves the formation of an organocopper compound (RCuX) which reacts with the other aryl reactant in a nucleophilic aromatic substitution. Alternative mechanisms do exist such as σ-bond metathesis.The classical Ullmann reaction is limited to electron deficient aryl halides and requires harsh reaction conditions. Modern variants of the Ullman reaction employing palladium and nickel have widened the substrate scope of the reaction and rendered reaction conditions more mild. Yields are generally still moderate, however. In organic synthesis this reaction is often replaced by palladium coupling reactions such as the Heck reaction, the Hiyama coupling and the Sonogashira coupling.In a variation of the Ullmann reaction, (2-bromovinyl)-benzene is reacted with imidazole in an ionic liquid, BMIMBF4*, to give N-(2-phenylvinyl)-imidazole. The reaction requires (L)-proline catalysis.".
- Ullmann_reaction thumbnail Ullmann_reaction.svg?width=300.
- Ullmann_reaction wikiPageID "2214609".
- Ullmann_reaction wikiPageLength "4753".
- Ullmann_reaction wikiPageOutDegree "42".
- Ullmann_reaction wikiPageRevisionID "681973152".
- Ullmann_reaction wikiPageWikiLink 1-butyl-3-methylimidazolium_tetrafluoroborate.
- Ullmann_reaction wikiPageWikiLink Alloy.
- Ullmann_reaction wikiPageWikiLink Aryl.
- Ullmann_reaction wikiPageWikiLink Benzene.
- Ullmann_reaction wikiPageWikiLink Biphenyl.
- Ullmann_reaction wikiPageWikiLink Bromine.
- Ullmann_reaction wikiPageWikiLink Catalysis.
- Ullmann_reaction wikiPageWikiLink Category:Carbon-carbon_bond_forming_reactions.
- Ullmann_reaction wikiPageWikiLink Category:Condensation_reactions.
- Ullmann_reaction wikiPageWikiLink Category:Name_reactions.
- Ullmann_reaction wikiPageWikiLink Copper.
- Ullmann_reaction wikiPageWikiLink Copper(I)-thiophene-2-carboxylate.
- Ullmann_reaction wikiPageWikiLink Coupling_reaction.
- Ullmann_reaction wikiPageWikiLink Electron_paramagnetic_resonance.
- Ullmann_reaction wikiPageWikiLink Fritz_Ullmann.
- Ullmann_reaction wikiPageWikiLink Halide.
- Ullmann_reaction wikiPageWikiLink Heck_reaction.
- Ullmann_reaction wikiPageWikiLink Hiyama_coupling.
- Ullmann_reaction wikiPageWikiLink Imidazole.
- Ullmann_reaction wikiPageWikiLink Ionic_liquid.
- Ullmann_reaction wikiPageWikiLink Irma_Goldberg.
- Ullmann_reaction wikiPageWikiLink Nitrobenzene.
- Ullmann_reaction wikiPageWikiLink Nucleophilic_aromatic_substitution.
- Ullmann_reaction wikiPageWikiLink Organic_synthesis.
- Ullmann_reaction wikiPageWikiLink Organocopper_compound.
- Ullmann_reaction wikiPageWikiLink Oxidative_addition.
- Ullmann_reaction wikiPageWikiLink Palladium.
- Ullmann_reaction wikiPageWikiLink Palladium-catalyzed_coupling_reactions.
- Ullmann_reaction wikiPageWikiLink Proline.
- Ullmann_reaction wikiPageWikiLink Radical_(chemistry).
- Ullmann_reaction wikiPageWikiLink Reaction_mechanism.
- Ullmann_reaction wikiPageWikiLink Salt_metathesis_reaction.
- Ullmann_reaction wikiPageWikiLink Sigma_bond.
- Ullmann_reaction wikiPageWikiLink Sonogashira_coupling.
- Ullmann_reaction wikiPageWikiLink Vinyl.
- Ullmann_reaction wikiPageWikiLink Wurtz–Fittig_reaction.
- Ullmann_reaction wikiPageWikiLink File:UllmannReaction.svg.
- Ullmann_reaction wikiPageWikiLink File:UllmannReactionWang2005.svg.
- Ullmann_reaction wikiPageWikiLink File:Ullmann_reaction.svg.
- Ullmann_reaction wikiPageWikiLinkText "Ullmann condensation".
- Ullmann_reaction wikiPageWikiLinkText "Ullmann coupling".
- Ullmann_reaction wikiPageWikiLinkText "Ullmann reaction".
- Ullmann_reaction wikiPageWikiLinkText "Ullmann".
- Ullmann_reaction name "Ullmann reaction".
- Ullmann_reaction namedafter Fritz_Ullmann.
- Ullmann_reaction type "Coupling reaction".
- Ullmann_reaction wikiPageUsesTemplate Template:Reactionbox.
- Ullmann_reaction wikiPageUsesTemplate Template:Reactionbox_Identifiers.
- Ullmann_reaction wikiPageUsesTemplate Template:Reflist.
- Ullmann_reaction subject Category:Carbon-carbon_bond_forming_reactions.
- Ullmann_reaction subject Category:Condensation_reactions.
- Ullmann_reaction subject Category:Name_reactions.
- Ullmann_reaction hypernym Reaction.
- Ullmann_reaction type Disease.
- Ullmann_reaction type Eponym.
- Ullmann_reaction type Reaction.
- Ullmann_reaction comment "The Ullmann reaction or Ullmann coupling is a coupling reaction between aryl halides and copper. The reaction is named after Fritz Ullmann, who derived it from a reaction developed by his wife, Irma Goldberg. A typical example is the coupling of 2 o-chloronitrobenzene reactants to form 2,2'-dinitrobiphenyl with a copper - bronze alloy.The traditional version of the Ullmann reaction requires harsh reaction conditions, and the reaction has a reputation for erratic yields.".
- Ullmann_reaction label "Ullmann reaction".
- Ullmann_reaction sameAs Q904703.
- Ullmann_reaction sameAs Ullmann-Reaktion.
- Ullmann_reaction sameAs واکنش_اولمان.
- Ullmann_reaction sameAs Rxc3xa9action_dUllmann.
- Ullmann_reaction sameAs Accoppiamento_di_Ullmann.
- Ullmann_reaction sameAs ウルマン反応.
- Ullmann_reaction sameAs Ullmann-reactie.
- Ullmann_reaction sameAs Reakcja_Ullmanna.
- Ullmann_reaction sameAs m.06wht6.
- Ullmann_reaction sameAs Q904703.
- Ullmann_reaction sameAs 乌尔曼反应.
- Ullmann_reaction wasDerivedFrom Ullmann_reaction?oldid=681973152.
- Ullmann_reaction depiction Ullmann_reaction.svg.
- Ullmann_reaction isPrimaryTopicOf Ullmann_reaction.