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Tetrakis(triphenylphosphine)palladium CAS 14221-01-3

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  • Appearance: Yellow powder
  • Purity: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Tetrakis(triphenylphosphine)palladium Supplier & Manufacturer

Basic Info

What is Tetrakis(triphenylphosphine)palladium?

Palladium carbon catalyst is a kind of commonly used hydrogenation catalyst and coupling catalyst, and it is widely used in organic synthesis Suzuki coupling reaction, Heck reaction and Sonogashira reaction. For a long time, homogeneous phosphorus ligand catalysts have been used in suzuki coupling reactions. Although homogeneous catalysts have high activity and selectivity, precious metals cannot be recovered after use, resulting in environmental pollution and waste of resources. In recent years, in the Suzuki coupling reaction, researchers have begun to use supported palladium catalysts such as palladium on carbon as catalysts for the synthesis of couplings. However, the substrates vary greatly, and a single palladium carbon cannot meet the needs of the reaction. Therefore, it is necessary to modify the palladium carbon to enhance its activity.

Tetrakis(triphenylphosphine)palladium is a compound with the molecular formula Pd[P(C6H5)3]4, often abbreviated as Pd(PPh3)4, or PdP4. It is a bright yellow crystalline solid that slowly turns brown on exposure to air. Tetrakis(triphenylphosphine)palladium is a complex with zero-valent palladium as the central atom and four triphenylphosphine as ligands, which is mainly used to catalyze C-C and C-B cross-coupling reactions. Through the coupling reaction catalyzed by palladium, many complex organic molecules including drugs can be synthesized. Three scientists Heck, Nagishi and Suzuki from the United States and Japan won the 2010 Nobel Prize in Chemistry for their outstanding achievements in this area. At present, tetrakis(triphenylphosphine)palladium, as a kind of important cross-coupling reaction catalyst, has been successfully used in the synthesis of some drugs, pesticides and organic functional molecules.

Tetrakis(triphenylphosphine)palladium Uses

Special catalyst for the synthesis of medication as well as chemical (Abamectin benzoate).
Extensively made use of in essential isomerization responses, side to side paired reaction stimulants.

Hydrosilation, isomerization, carbonylation, oxidation, C-C bond formation as well as various other reactions. For combining response, Heck reaction, Sonogashira reaction, StChemicalbookille response, Suzuki response. Terakis (triphenylphosphine) palladium (0).

Pd(PPh3)4 is widely used as a catalyst in palladium-catalyzed coupling reactions. Among the most important applications are Heck reactions, Suzuki couplings, Stille reactions, Sonogashira coupling reactions, and Negishi couplings. These coupling reaction processes start with two consecutive ligand dissociation processes, followed by oxidative addition of aryl halides to the zero-valent palladium atom center:

Pd(PPh3)4 + ArBr → PdBr(Ar)(PPh3)2 + 2 PPh3

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Application of Tetrakis(triphenylphosphine)palladium

Tetrakis (triphenylphosphine) palladium (0) is a palladium complex, commonly known as catalyst B or catalyst No. 2, is a special catalyst for the synthesis of abamectin benzoate, and can also be widely used in The following areas: important isomerization reactions – such as isomerization of arenes and alkenes; carbonylation, hydrosilylation, oxidation, C-C bond formation, alkyne ring trimerization; coupling reactions – such as arylates with Coupling reactions of aryl halides, etc. Its application examples are as follows:

Tetrakis (triphenylphosphine) palladium can be used as catalyst for synthesizing a kind of diaryl acetylene, and this method is under protective atmosphere, iodo arene and diethoxy phosphonoacetylene in containing tetrakis (triphenylphosphine) Carry out Sonogashira coupling reaction I in the solution system of palladium, cuprous iodide and diisopropylamine, obtain 1-aryl-1′-diethoxyphosphonoacetylene; Said 1-aryl-1′-diethyl Oxyphosphonoacetylene and bromoarene are subjected to Sonogashira coupling reaction II in a solution system containing tetrakistriphenylphosphine palladium, cuprous iodide and diisopropylamine under the action of potassium tert-butoxide, to obtain that product. During the coupling reaction, the molar ratio of iodoarene to diethoxyphosphonoacetylene, tetrakistriphenylphosphine palladium, cuprous iodide and diisopropylamine is 1.2:0.8~1.2:0.04~0.06:0.04~0.06 :3~4,; the most preferred molar ratio is 1.2:1:0.05:0.05:3.5.

Preparation of Tetrakis(triphenylphosphine)palladium

Tetrakis(triphenylphosphine)palladium was first discovered by Lamberto Malatesta’s group in Milan in 1960, when the compound was formed by the reduction reaction of sodium chloropalladate and hydrazine in the presence of phosphine. This compound is commercially available and can be obtained by a two-step reaction from a compound precursor of divalent palladium:

PdCl2 + 2 PPh3 → cis-PdCl2(PPh3)2

cis-PdCl2(PPh3)2 + 2 PPh3 + 2.5 N2H4 → Pd(PPh3)4 + 0.5 N2 + 2 N2H5+Cl-

The two steps can be carried out by a one-pot synthesis method, and the intermediate cis-PdCl2(PPh3)2 does not need to be isolated and purified. Hydrazine can be replaced by other reducing agents. The compound is sensitive to air, and the crude product can be washed with methanol to obtain a relatively pure yellow powder. The compound is usually stored in an argon atmosphere.

Reference

  1. Tetrakis(triphenylphosphine)palladium(0) – WikiPedia
  2. Synthesis of some phenanthrene compounds catalyzed by tetrakis(triphenylphosphine)

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