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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.

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  • 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, 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 , 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. (en)
  • De Heck-Matsuda-reactie is een palladium-gekatalyseerde koppelingsreactie tussen een aryldiazoniumzout (als alternatief voor arylhalogeniden of aryltriflaten) en een alkeen: Het gebruik van een aromatische diazoniumverbinding levert in zekere zin een voordeel op ten opzichte van analoge arylhalogeniden, omdat geen fosfines als liganden nodig zijn. Derhalve hoeft de reactie niet in anaerobe omstandigheden te verlopen, hetgeen vooral voordelen oplevert voor de praktische uitvoering van de synthese. Daarenboven kan de Heck-Matsuda-reactie uitgevoerd worden in de aan- of afwezigheid van een base. Als variant wordt de intramoleculaire Heck-Matsuda-reactie aangewend ter synthese van heterocyclische verbindingen: (nl)
  • A reação de Heck-Matsuda (reação HM) é uma reação de acoplamento de grupos aril a alcenos catalisada por paládio, que usa sais de arenodiazônio como uma alternativa aos haletos de arila e triflatos que caracterizam outro acoplamento (reação de Heck). O uso de sais de arenodiazônio apresenta algumas vantagens em relação aos eletrófilos haletos de arila tradicionais. Por exemplo, o uso de fosfinas como ligantes do catalisador não é necessário e, portanto, a realização da reação não requer condições aeróbicas, o que a torna mais prática. Além disso, a reação pode ser realizada com ou sem base e geralmente é mais rápida que o acoplamento de Heck tradicional: Álcoois alílicos, alcenos conjugados, heterociclos insaturados e alcenos não ativados podem ser arilados com sais de arenodiazônio usando catalisadores simples como acetato de paládio (Pd(OAc)2) ou tris(dibenzilidenoacetona)dipaládio(0) (Pd2dba3) no ar ou em solventes inócuos e adequados à temperatura ambiente. Além da variante intermolecular da reação de Heck-Matsuda, processos de ciclização intramolecular também foram desenvolvidos para a construção de diversos heterociclos de oxigênio e nitrogênio. O ciclo catalítico para a reação de arilação de Heck-Matsuda tem quatro etapas principais: adição oxidativa, inserção migratória ou carbopaladação, β-eliminação sin e eliminação redutiva. Esse ciclo proposto, envolvendo paládio catiônico com sais de arenodiazônio, foi reforçado por estudos com espectrometria de massa (ESI) de Correia e seus colaboradores. Esses resultados também mostram as interações complexas que ocorrem na esfera de coordenação do paládio durante a reação de Heck com o sal de arenodiazônio. (pt)
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  • 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. (en)
  • De Heck-Matsuda-reactie is een palladium-gekatalyseerde koppelingsreactie tussen een aryldiazoniumzout (als alternatief voor arylhalogeniden of aryltriflaten) en een alkeen: Het gebruik van een aromatische diazoniumverbinding levert in zekere zin een voordeel op ten opzichte van analoge arylhalogeniden, omdat geen fosfines als liganden nodig zijn. Derhalve hoeft de reactie niet in anaerobe omstandigheden te verlopen, hetgeen vooral voordelen oplevert voor de praktische uitvoering van de synthese. Daarenboven kan de Heck-Matsuda-reactie uitgevoerd worden in de aan- of afwezigheid van een base. (nl)
  • A reação de Heck-Matsuda (reação HM) é uma reação de acoplamento de grupos aril a alcenos catalisada por paládio, que usa sais de arenodiazônio como uma alternativa aos haletos de arila e triflatos que caracterizam outro acoplamento (reação de Heck). Álcoois alílicos, alcenos conjugados, heterociclos insaturados e alcenos não ativados podem ser arilados com sais de arenodiazônio usando catalisadores simples como acetato de paládio (Pd(OAc)2) ou tris(dibenzilidenoacetona)dipaládio(0) (Pd2dba3) no ar ou em solventes inócuos e adequados à temperatura ambiente. (pt)
rdfs:label
  • Heck–Matsuda reaction (en)
  • Heck-Matsuda-reactie (nl)
  • Reação de Heck-Matsuda (pt)
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