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Palladium Catalysts [Cross-coupling Reaction using Transition Metal Catalysts]

 The study of coupling reactions using organopalladium complexes has been advanced as well as that using organonickel complexes. Generally, the reactivity of organopalladium complexes is lower compared with organonickel complexes. However, they have higher chemical stability for oxidations and this makes them easy to use. Therefore, palladium complexes are most commonly used for cross-coupling reactions.

(1) Palladium complexes generally used in cross coupling reactions
 Palladium-phosphine complexes are well used in cross-coupling reactions and commercially available. Pd(PPh3)4 and PdCl2(PPh3)2 are used without any treatment. Also, palladium catalysts are used prepared in situ from the precursors such as Pd(OAc)2 and Pd2(dba)3·CHCl3, with appropriate amounts of phosphines. When using divalent palladium complexes such as Pd(OAc)2, once they are reduced to zero-valent palladium species by some organometallic reagents, phosphines and amines, then their catalytic reactions can start.
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(2) Higher activity palladium catalysts
 Generally, cross coupling reactions are promoted by using electron-rich and sterically hindered ligands. For example, palladium catalysts when coordinated by tertiary alkyl phosphines such as the tert-butyl group, cyclohexyl group and so on are used, show high catalytic activities in cross-coupling reactions. They are effective to use when low reactive aryl chlorides or sterically hindered aromatic halides are employed as reagents. The monomer state of sterically hindered alkyl phosphines is chemically unstable, but they are stabilized by coordinating them with palladium complexes.
 Recently, N-heterocarbene (NHC) ligands have been used for cross-coupling reactions because they activate palladium catalysts more effectively than tertiary alkyl phosphines. Palladium-NHC complexes show not only high activity but also high structual stability. In addition, they keep their complex formation without decomposition even after work-up, which is an advantage because it makes removing these complexes easy.

(3) Palladacycle catalysts
 In some cases the active palladium species can’t be efficiently prepared by the combination of palladium complexes and ligands. To solve this problem, palladacycle catalysts have been developed and used for more efficient preparation of active palladium species. As a property, they easily release the coordinated ligand with treatment of some bases, and afford the related zero-valent active palladium species. On the other hand, they form structurally stable complexes caused by their cyclic structures constructed of the ligand with intramolecular coordinating ability and the palladium species. In addition, their catalytic ability is improved by the addition of bases and they show high turnover frequency.
A1424
Palladium(II) Acetate
A1479
Allylpalladium(II) Chloride Dimer
B1374
Bis(dibenzylideneacetone)palladium(0)
B1667
Bis(triphenylphosphine)palladium(II) Dichloride
B1668
Bis(benzonitrile)palladium(II) Dichloride
B1676
Bis(acetonitrile)palladium(II) Dichloride
B2016
[1,2-Bis(diphenylphosphino)ethane]palladium(II) Dichloride
B2018
Bis(2,4-pentanedionato)palladium(II)
B2026
Bis(tri-o-tolylphosphine)palladium(II) Dichloride
B2042
Bis(triphenylphosphine)palladium(II) Diacetate
B2055
Bis(tricyclohexylphosphine)palladium(II) Dichloride
B2064
[1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) Dichloride Dichloromethane Adduct
B3160
[1,1'-Bis(di-tert-butylphosphino)ferrocene]palladium(II) Dichloride
B3161
Bis(tri-tert-butylphosphine)palladium(0)
B3224
Bis[1,2-bis(diphenylphosphino)ethane]palladium(0)
B4837
Bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]palladium(0)
C2372
Chloro[[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](N,N-dimethylbenzylamine)palladium(II)] (This product is unavailable in the U.S.)
C2387
Chloro[[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](acetanilide)palladium(II)] (This product is unavailable in the U.S.)
C2406
Chloro[[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](N,N-dimethyl-3,5-dimethoxybenzylamine)palladium(II)] (This product is unavailable in the U.S.)
C2734
Chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II)
D3704
[Di-tert-butyl(chloro)phosphine]palladium(II) Dichloride Dimer
D3706
Dihydrogen Di-μ-chlorotetrakis(di-tert-butylphosphinito)dipalladate
D3806
Di-μ-chlorobis[5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl]palladium(II) Dimer
D3807
Di-μ-chlorobis[5-hydroxy-2-[1-(hydroxyimino)ethyl]phenyl]palladium(II) Dimer
D3847
Di-μ-chlorobis[2-[(dimethylamino)methyl]phenyl-C,N]dipalladium(II)
D4112
Di-μ-chlorobis[2-[(dimethylamino)methyl]-4,6-dimethoxyphenyl-C,N]dipalladium(II)
D4191
Di-μ-chlorobis(2'-amino-1,1'-biphenyl-2-yl-C,N)dipalladium(II)
D4333
Dichloro[9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene]palladium(II)
P1425
Poly[N-isopropylacrylamide-co-4-(diphenylphosphino)styrene] Palladium(II) Dichloride (ratio, acrylamide:phosphine=20:2)
P1489
Palladium(II) Chloride
P1490
Palladium 5% on Carbon (wetted with ca. 55% Water)
P1491
Palladium 10% on Carbon (wetted with ca. 55% Water)
P1785
Palladium 10% on Carbon (wetted with ca. 55% Water) [Useful catalyst for coupling reaction, etc.]
P1870
Palladium(II) Trifluoroacetate
P1944
Poly(methylphenyl)silane supported Palladium/Alumina Hybrid Catalyst [=Pd / (PSi-Al2O3)]
P2017
Palladium(II)(π-cinnamyl) Chloride Dimer
P2106
Palladium(II) Acetate Trimer
P2161
Palladium(II) Acetate (Purified)
P2238
Palladium 5% on Alumina
S0540
Sodium Tetrachloropalladate(II)
T1350
Tetrakis(triphenylphosphine)palladium(0)
T2184
Tris(dibenzylideneacetone)dipalladium(0)
T3023
Tetrakis(acetonitrile)palladium(II) Bis(trifluoromethanesulfonate)

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