Palladium-carbon catalyst is a commonly used hydrogenation catalyst and coupling catalyst, which is widely used in organic synthesis Suzuki coupling reaction, Heck reaction and Sonogashira reaction. Although homogeneous catalysts have higher activity and selectivity, after use, precious metals cannot be recovered, resulting in environmental pollution and resource waste. In recent years, in the Suzuki coupling reaction, researchers have begun to use supported palladium catalysts such as palladium carbon as a catalyst to synthesize the coupling. But the substrates vary widely, 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 of the formula Pd[P(C6H5)3]4, often abbreviated as Pd(PPh3)4, or PdP4. Tetrakis(triphenylphosphine) palladium is a complex with zero-valent palladium as the central atom and four triphenylphosphine as ligands, and is mainly used to catalyze C-C and C-B cross-coupling reactions. Through the palladium-catalyzed coupling reaction, many organic complex molecules, including drugs, can be synthesized. Three scientists from the United States and Japan, Heck, Nagishi, and Suzuki, won the 2010 Nobel Prize in Chemistry for their outstanding achievements in this area. At present, tetrakis (triphenylphosphine) palladium, as an important catalyst for cross-coupling reaction, has been successfully used in the synthesis of some drugs, pesticides and organic functional molecules.
Fine Powder or Platelets
Bright yellow to khaki
7: reacts slowly with moisture/water
Light Sensitive/Air Sensitive
Application of Tetrakis(triphenylphosphine)Palladium
Tetrakis(triphenylphosphine)palladium(0) is a complex of palladium, commonly known as catalyst B or catalyst No. 2. It is a special catalyst for the synthesis of methylaminoavermectin 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. Examples of its application are as follows: Tetrakis (triphenylphosphine) palladium can be used as a catalyst to synthesize a diaryl acetylene. The method is that under protective atmosphere, iodoaromatic hydrocarbons and diethoxy phosphono acetylene are mixed with tetrakis Throughout the coupling response, the molar ratio of iodoaromatic hydrocarbons to diethoxyphosphonoacetylene, tetrakistriphenylphosphine palladium, cuprous iodide as well as diisopropylamine is 1.2:0.8 ～ 1.2:0.04 ～ 0.06:0.04 ～ 0.06: 3 ～ 4,; one of the most favored molar proportion is 1.2:1:0.05:0.05:3.5.
Synthesis of Tetrakis(triphenylphosphine)Palladium
Method 1: In this method, the tetrakis (triphenylphosphine) palladium synthesis method mainly involves three-step reactions:
1) PdCl2 undergoes coordination substitution reaction with triphenylphosphine in DMF to generate trans-dichlorobis(triphenylphosphine)palladium(II) intermediate;
2) Hydrazine hydrate reduces divalent palladium in trans-dichlorobis(triphenylphosphine)palladium(II) to zero-valent palladium;
3) Finally, two chlorines leave, and the central atom is then coordinated with two triphenylphosphine to form tetrakis (triphenylphosphine) palladium.
These three-step reactions are carried out sequentially in the same reactor, and the yield can reach more than 95% by controlling appropriate reaction conditions and feeding ratios. Since the palladium in tetrakis(triphenylphosphine)palladium is in a zero-valent state and is easily oxidized and discolored, the entire operation should avoid an oxidative environment, and the product should be stored in an inert atmosphere such as nitrogen.
Method 2: Using palladium dichloride and triphenylphosphine as reaction raw materials, A as solvent and B as reducing agent, tetrakis(triphenylphosphine) palladium was synthesized by oil bath heating reaction, and the product yield was close to 95%. The preparation process conditions are as follows: the reaction temperature is 140 °C, the reduction temperature is 105 °C, the molar ratio of PRh3 and PdCl2 is 4.5:1, the molar ratio of solvent B and PdCl2 is 4:1, and the feeding method is to first dissolve the two separately and then carry out The reaction is carried out by mixing, and the post-processing method is washing with Y reagent, nitrogen pressure filtration, and vacuum packaging for low temperature storage.
Commonly Used Catalyst---Tetrakis (triphenylphosphine) Palladium
As an essential shift metal catalyst,
Pd(PPh3)4 can be used to militarize different responses such as coupling, oxidation, reduction, removal, reformation, and isomerization. Its catalytic effectiveness is really high, and also it can militarize numerous responses that are tough to take place under the action of similar catalysts. Catalytic carbon-carbon bond development As an important catalyst, Pd(PPh3)4 is often used to catalyze the coupling reaction (Cross-Coupling Reaction) and is an important method for constructing carbon-carbon bonds, which is characterized by mild catalytic conditions. For example, under the combined action of Pd(PPh3)4 and Ag2O, phenylboronic acid was directly reacted with aromatic halogenated hydrocarbons to generate biphenyls in 90% yield (Equation 1). In addition to phenylboronic acid and halides, magnesium reagents, zinc reagents, tin reagents, silicon compounds, etc. can be used as substrates for the coupling reaction.
Under the catalysis of Pd(PPh3)4, halogenated aromatic hydrocarbons, etc. can directly react with olefin derivatives to form styrene derivatives (the reaction type is Heck reaction) (Equation 2).
Pd(PPh3)4 can also catalyze the coupling of alkyne compounds and halides (Sonogashira reaction). During the reaction, alkyne hydrogen and halogen element form hydrogen halide (or neutralize with alkali) and leave, and the product is alkyne. Derivatives (Formula 3).
At the same time, under the catalysis of Pd(PPh3)4, the C-H bond on the aromatic ring can be activated, and then it can react with halogenated compounds, tin compounds, etc. to remove a molecule of hydrogen halide or stannane to form a C-C bond (Formula 4 ).
In addition, since Pd(PPh3)4 can catalyze the formation of various C-C bonds, it is possible to construct reactions catalyzed by multiple sites at the same time, such as intermolecular cyclization reactions (Eq. 5).
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