Palladium compounds: Difference between revisions
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[[Palladium]] forms a variety of compounds, typically with oxidation state Pd<sup>0</sup> or Pd<sup>2+</sup>. Palladium compounds are frequently used as catalysts in [[cross-coupling reaction]]s such as the [[Sonogashira coupling]] and [[Suzuki reaction]]. |
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#REDIRECT [[Palladium#Compounds]] |
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==Ionic compounds== |
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[[File:Pd(OAc)2.jpg|thumb|Palladium(II) acetate, {{Chem2|Pd(OAc)2}}]] |
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Most ionic compounds of palladium involve the Pd<sup>2+</sup> oxidation state. [[Palladium(II) chloride]] is a starting point in the synthesis of other palladium compounds and complexes.<ref name="1993 OrgSyn Suzuki">{{OrgSynth |title = Palladium-catalyzed reaction of 1-alkenylboronates with vinylic halides: (1Z,3E)-1-Phenyl-1,3-octadiene |collvol = 8 |collvolpages = 532 |author1-link=Norio Miyaura |author1= Miyaura, Norio |author2 = Suzuki, Akira |name-list-style=amp |year = 1993 |prep = cv8p0532}}</ref> [[Palladium(II) acetate]] plus [[triphenylphosphine]] is used as a catalyst in organic synthesis.<ref name="1995 Suzuki review">{{cite journal |last1=Miyaura |first1=Norio |author1-link=Norio Miyaura |last2=Suzuki |first1=Akira |author2-link=Akira Suzuki |title=Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. |journal=[[Chemical Reviews]] |year=1995 |volume=95 |issue=7 |pages=2457–2483 |doi=10.1021/cr00039a007}}</ref> |
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==Coordination chemistry== |
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[[File:Dichlorobis(triphenylphosphine)palladium(II).jpg|thumb|Bis(triphenylphosphine)palladium chloride, {{Chem2|PdCl2(PPh3)2}}]] |
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Coordination compounds of palladium contain ligands coordinated to a central Pd<sup>0</sup> or Pd<sup>2+</sup> center. They are typically synthesized by adding ligands to an ionic palladium compound. For example, [[acetonitrile]], [[benzonitrile]], or [[triphenylphosphine]] may be coordinated to [[palladium(II) chloride]] ({{Chem2|PdCl2}}) to form [[bis(acetonitrile)palladium dichloride]] ({{Chem2|PdCl2(NCC6H5)2}}), [[bis(benzonitrile)palladium dichloride]] ({{Chem2|PdCl2(PPh3)2}}), or [[bis(triphenylphosphine)palladium chloride]] ({{Chem2|PdCl2(PPh3)2}}), respectively. Many other more exotic ligands form a large variety of palladium-phosphine catalysts, such as [[1,1'-bis(diphenylphosphino)ferrocene]] (dppf) to form [[(1,1'-Bis(diphenylphosphino)ferrocene)palladium(II) dichloride|[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride]] ({{Chem2|PdCl2(dppf)}}). |
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Bis(triphenylphosphine)palladium chloride, which contains palladium as Pd<sup>2+</sup>, may be reduced using [[hydrazine]] in the presence of triphenylphosphine to form [[tetrakis(triphenylphosphine)palladium(0)]] ({{Chem2|Pd(PPh3)4}}), which contains Pd<sup>0</sup>.<ref>{{cite book | journal = [[Inorg. Synth.]] | volume = 13 | pages = 121–124 | first1= D. R.|last1= Coulson | doi = 10.1002/9780470132449.ch23 | year = 1972 | last2 = Satek | first2 = L. C. | last3 = Grim | first3 = S. O. | chapter = Tetrakis(triphenylphosphine)palladium(0) | title = Inorganic Syntheses | isbn = 978-0-470-13244-9}}</ref> |
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==Organopalladium chemistry== |
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{{Main|Organopalladium chemistry}} |
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==Catalysis== |
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Both ionic and coordination palladium compounds are frequently used to catalyze [[cross-coupling reaction]]s. For the [[Suzuki reaction]], commonly used catalysts include [[Tetrakis(triphenylphosphine)palladium(0)|{{Chem2|Pd(PPh3)4}}]], [[Bis(triphenylphosphine)palladium chloride|{{Chem2|PdCl2(PPh3)2}}]],<ref name="1993 OrgSyn Suzuki"/> [[(1,1'-Bis(diphenylphosphino)ferrocene)palladium(II) dichloride|{{Chem2|PdCl2(dppf)}}]], as well as [[Palladium(II) acetate|{{Chem2|Pd(OAc)2}}]] plus [[triphenylphosphine]] ({{Chem2|PPh3}}).<ref name="1995 Suzuki review"/> A large variety of phosphine-based ligands may be used in palladium catalysts. Bulky, electron-rich ligands such as [[tris(2,4,6-trimethoxyphenyl)phosphine]] result in catalysts that are more reactive in the [[oxidative addition]] step and can catalyze the Suzuki reaction of [[aryl chloride]]s, which are typically unreactive.<ref>{{cite journal |last1=Reimann |first1=Sebastian |last2=Ehlers |first2=Peter |last3=Sharif |first3=Muhammad |last4=Spannenberg |first4=Anke |last5=Langer |first5=Peter |title=A general protocol for the efficient synthesis of polyarylated benzenes by multiple Suzuki-Miyaura reactions of polychlorinated benzenes |journal=[[Tetrahedron (journal)|Tetrahedron]] |year=2016 |volume=72 |issue=8 |pages=1083–1094 |doi=10.1016/j.tet.2016.01.010}}</ref> |
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==See also== |
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*[[:Category:Palladium compounds]] |
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*[[Nickel compounds]] |
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*[[Platinum compounds]] |
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==References== |
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{{reflist}} |
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[[Category:Palladium compounds| ]] |
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Revision as of 17:35, 21 March 2024
Palladium forms a variety of compounds, typically with oxidation state Pd0 or Pd2+. Palladium compounds are frequently used as catalysts in cross-coupling reactions such as the Sonogashira coupling and Suzuki reaction.
Ionic compounds
2.jpg)
Most ionic compounds of palladium involve the Pd2+ oxidation state. Palladium(II) chloride is a starting point in the synthesis of other palladium compounds and complexes.[1] Palladium(II) acetate plus triphenylphosphine is used as a catalyst in organic synthesis.[2]
Coordination chemistry
palladium(II).jpg)
Coordination compounds of palladium contain ligands coordinated to a central Pd0 or Pd2+ center. They are typically synthesized by adding ligands to an ionic palladium compound. For example, acetonitrile, benzonitrile, or triphenylphosphine may be coordinated to palladium(II) chloride (PdCl2) to form bis(acetonitrile)palladium dichloride (PdCl2(NCC6H5)2), bis(benzonitrile)palladium dichloride (PdCl2(PPh3)2), or bis(triphenylphosphine)palladium chloride (PdCl2(PPh3)2), respectively. Many other more exotic ligands form a large variety of palladium-phosphine catalysts, such as 1,1'-bis(diphenylphosphino)ferrocene (dppf) to form [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (PdCl2(dppf)).
Bis(triphenylphosphine)palladium chloride, which contains palladium as Pd2+, may be reduced using hydrazine in the presence of triphenylphosphine to form tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4), which contains Pd0.[3]
Organopalladium chemistry
Catalysis
Both ionic and coordination palladium compounds are frequently used to catalyze cross-coupling reactions. For the Suzuki reaction, commonly used catalysts include Pd(PPh3)4, PdCl2(PPh3)2,[1] PdCl2(dppf), as well as Pd(OAc)2 plus triphenylphosphine (PPh3).[2] A large variety of phosphine-based ligands may be used in palladium catalysts. Bulky, electron-rich ligands such as tris(2,4,6-trimethoxyphenyl)phosphine result in catalysts that are more reactive in the oxidative addition step and can catalyze the Suzuki reaction of aryl chlorides, which are typically unreactive.[4]
See also
References
- ^ a b Miyaura, Norio & Suzuki, Akira (1993). "Palladium-catalyzed reaction of 1-alkenylboronates with vinylic halides: (1Z,3E)-1-Phenyl-1,3-octadiene". Organic Syntheses; Collected Volumes, vol. 8, p. 532.
- ^ a b Miyaura, Akira; Suzuki (1995). "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds". Chemical Reviews. 95 (7): 2457–2483. doi:10.1021/cr00039a007.
- ^ Coulson, D. R.; Satek, L. C.; Grim, S. O. (1972). "Tetrakis(triphenylphosphine)palladium(0)". Inorganic Syntheses. Vol. 13. pp. 121–124. doi:10.1002/9780470132449.ch23. ISBN 978-0-470-13244-9.
{{cite book}}:|journal=ignored (help) - ^ Reimann, Sebastian; Ehlers, Peter; Sharif, Muhammad; Spannenberg, Anke; Langer, Peter (2016). "A general protocol for the efficient synthesis of polyarylated benzenes by multiple Suzuki-Miyaura reactions of polychlorinated benzenes". Tetrahedron. 72 (8): 1083–1094. doi:10.1016/j.tet.2016.01.010.