Merck
CN

216666

Sigma-Aldrich

四(三苯基膦)钯(0)

99%

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别名:
Pd(PPh3)4, 四(三苯基膦)钯
线性分子式:
Pd[(C6H5)3P]4
CAS号:
分子量:
1155.56
Beilstein:
6704828
EC 号:
MDL编号:
PubChem化学物质编号:
NACRES:
NA.22

质量水平

检测方案

99%

形式

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

储存温度

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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一般描述

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.

应用

四(三苯基膦)钯(0)可用作以下反应的催化剂:



  • Negishi偶联反应(反应式1), 铃木偶联反应(反应式2),Stille偶联反应(反应式3),以及Sonogashira偶联反应(反应式4),以及Buchwald-Hartwig氨基化反应(反应式5)
  • 碘化乙烯的羰基化反应(反应式6)
  • 芳基溴化物的还原反应(反应式7)
  • 碳-锡键形成反应(反应式8)
Triphenyl Phosphine Catalyst

象形图

Exclamation mark

警示用语:

Warning

危险声明

危险分类

Acute Tox. 4 Oral

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)


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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. The color of Product 216666, Pd tetrakis(triphenylphosphine)Cl was a yellow or gold color, but now my material has turned a tan, brown, or green color.  Is it still good to use?

    A change in color of the material indicates oxidation and it will no longer be active as a catalyst.

  4. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

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  6. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Hong-Lei Xu et al.
Nature communications, 11(1), 5286-5286 (2020-10-22)
Sandwich-type clusters with the planar fragment containing a heterometallic sheet have remained elusive. In this work, we introduce the [K(2,2,2-crypt)]4{(Ge9)2[η6-Ge(PdPPh3)3]} complex that contains a heterometallic sandwich fragment. The title compound is structurally characterized by means of single-crystal X-ray diffraction, which
Alami, F.; Ferri, F. et al.
Tetrahedron Letters, 34, 6403-6403 (1993)
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)
Miyaura, M.; Suzuki, A.
Journal of the American Chemical Society, 107, 972-972 (1985)
Azizian, H.; Eaborn, C.; Pidcock, A.
Journal of Organometallic Chemistry, 215, 49-49 (1981)

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