216666

Tetrakis(triphenylphosphine)palladium(0)

99%

• Synonym(s): Palladium-tetrakis(triphenylphosphine), Pd(PPh₃)₄
• Linear Formula: Pd[(C₆H₅)₃P]₄
• CAS Number: 14221-01-3
• Molecular Weight: 1155.56
• Beilstein/REAXYS Number: 6704828
• EC Number: 238-086-9
• MDL number: MFCD00010012
• UNSPSC Code: 12352103
• PubChem Substance ID: 24852971
• NACRES: NA.22

Properties

• 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
• parameter: air sensitive
• 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

Description

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

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

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)

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)