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Tetrakis(triphenylphosphine)palladium(0)

99%

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Synonym(s):
Palladium-tetrakis(triphenylphosphine), Pd(PPh3)4
Linear Formula:
Pd[(C6H5)3P]4
CAS Number:
Molecular Weight:
1155.56
Beilstein:
6704828
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

form

solid

reaction suitability

core: palladium
reaction type: Cross Couplings
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst
reaction type: Buchwald-Hartwig Cross Coupling Reaction

storage temp.

2-8°C

SMILES string

[Pd].c1ccc(cc1)P(c2ccccc2)c3ccccc3.c4ccc(cc4)P(c5ccccc5)c6ccccc6.c7ccc(cc7)P(c8ccccc8)c9ccccc9.c%10ccc(cc%10)P(c%11ccccc%11)c%12ccccc%12

InChI

1S/4C18H15P.Pd/c4*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h4*1-15H;

InChI key

NFHFRUOZVGFOOS-UHFFFAOYSA-N

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This Item
697265208671752762
PPh3 Pd G2

Sigma-Aldrich

752762

PPh3 Pd G2

form

solid

form

crystals

form

solid

form

solid

reaction suitability

core: palladium, reaction type: Cross Couplings, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst
reaction type: Buchwald-Hartwig Cross Coupling Reaction

reaction suitability

core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Cross Couplings, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst

reaction suitability

core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst

reaction suitability

core: palladium, reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Cross Couplings, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

General description

Palladium-tetrakis(triphenylphosphine) (Pd(PPh3)4) iscoordination complex of palladium and is widely used palladium cross-coupling catalyst. These applications include Negishi coupling, Suzuki coupling, Stille coupling, Sonogashira coupling, and Buchwald-Hartwig amination reactions.




Tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) is a commonly used palladium(0) complex in chemical synthesis. It plays a vital role as a catalyst in various organic reactions, especially C-C, C-N, C-O, and C-heteroatom cross-coupling reactions. Pd(PPh3)4 finds extensive application in carbon-carbon bond-forming reactions such as the famous Heck, Suzuki-Miyaura, and Stille reactions. These reactions involve the coupling of aryl, alkyl, or vinyl halides with other organic compounds to yield valuable products. The catalytic cycle involves the oxidative addition of the organic halide to palladium(0), transmetalation with a suitable organometallic reagent or boronic acid, and reductive elimination to form the desired product. Pd(PPh3)4 has also been utilized in various other transformations including allylic substitutions, nucleophilic additions to alkenes and alkynes, and cycloadditions.

Application

Tetrakis(triphenylphosphine)palladium(0) can be used as a catalyst in:



  • Negishi coupling (eq. 1), Suzuki coupling (eq. 2), Stille coupling (eq. 3), Sonogashira coupling reaction (eq. 4), and Buchwald-Hartwig amination reaction (eq. 5)
  • The carbonylation of vinyl iodides (eq. 6)
  • The reduction reaction of aryl bromides (eq. 7)
  • Carbon-tin bond formation (eq. 8)
Triphenyl Phosphine Catalyst

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Palladium-catalyzed formylation of organic halides with carbon monoxide and tin hydride.
V P Baillargeon et al.
Journal of the American Chemical Society, 108(3), 452-461 (1986-02-01)
Milstein, D.; Still, J. K.
Journal of the American Chemical Society, 101, 4992-4992 (1979)
Azizian, H.; Eaborn, C.; Pidcock, A.
Journal of Organometallic Chemistry, 215, 49-49 (1981)
Kotora, M; Xu, C.; Negishi, E.
The Journal of Organic Chemistry, 62, 8957-8957 (1997)
Miyaura, M.; Suzuki, A.
Journal of the American Chemical Society, 107, 972-972 (1985)

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