| Revision as of 20:27, 1 April 2011 editV8rik (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers16,348 editsm The Heck-Matsuda Reaction of an arenediazonium salt with an alkene← Previous edit | Latest revision as of 19:50, 27 May 2019 edit undoChristian75 (talk | contribs)Extended confirmed users, New page reviewers, Pending changes reviewers, Rollbackers114,672 edits {{R with history}} | ||
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| ]'''Palladium compounds''' are used as a '''catalyst''' in many coupling reactions, usually as a ]. Examples include: | |||
| {{R with history}} | |||
| * ] between ]s and aryl halides | |||
| * ] between aryl halides and ] | |||
| * ] between ]s and ]s | |||
| * ] between organohalides and ]s | |||
| * ] between aryl halides and ]s, with ] as a co-catalyst | |||
| * ] between an organohalide and an ] | |||
| * The ] of an aryl halide with an ] | |||
| * The ] of an arenediazonium salt with an alkene | |||
| Typical palladium catalysts used include the following compounds: | |||
| * ] | |||
| * ] | |||
| * ] | |||
| * palladium(II) dichloride]] | |||
| Unoptimized reactions typically use 10-15 mol% of palladium; where optimized, catalyst loadings can be on the order of 0.1 mol % or below. Many exotic ligands and chiral catalysts have been reported, but they are largely not available commercially, and do not find widespread use. Much work is being done on replacing the phosphine ligands with other classes, such as Arduengo-type ] complexes, as the phosphine ligands are typically oxygen sensitive (easily oxidized), and are labile (requiring additional free ligands). | |||
| With these reactions becoming ubiquitous, there has been interest in better techniques for removing the palladium catalyst. Metal scavengers such as Smopex<ref>http://www.alfa.com/en/GP100w.pgm?DSSTK=044710</ref> or resins such as QuadruPure<ref>http://www.sigmaaldrich.com/chemistry/drug-discovery/medicinal-chemistry/quadrapure.html</ref> and ISOLUTE<ref>http://www.biotage.com/DynPage.aspx?id=36161</ref> promise more efficient separation than ordinary ]. | |||
| In 2010, the ] was awarded to ], ] and ] for their work on palladium-catalyzed cross couplings in organic synthesis.<ref>http://nobelprize.org/nobel_prizes/chemistry/laureates/2010/</ref> | |||
| ==See also== | |||
| * ] | |||
| ==References== | |||
| <references/> | |||
| ] | |||
| ] | |||
| ] | |||
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