Tetrakis(triphenylphosphine)palladium, with the chemical formula Pd [P (C6H5) 3] 4, CAS 14221-01-3, commonly abbreviated as PdP4 or Pd (PPh3) 4, is an important chemical substance with wide applications in catalysis. Under normal temperature and pressure, it is usually a green yellow or yellow crystal/powder with a certain luster. This color is due to the special electronic arrangement formed by the binding of palladum atoms in its molecular structure with four triphenylphosphine ligands. Its shape may vary depending on the preparation method and storage conditions, for example, sometimes it may appear as a fine powder, and sometimes it may form larger crystal particles. It is difficult to dissolve in water and ether solvents, but soluble in various organic solvents such as benzene, toluene, dichloromethane, chloroform, dimethylformamide (DMF), tetrahydrofuran (THF), etc. It has moderate solubility in benzene, dichloromethane, and chloroform, while its solubility in solvents such as acetone, tetrahydrofuran, and acetonitrile is relatively small. This difference in solubility makes tetratriphenylphosphine palladum have broad application prospects in organic synthesis and catalytic reactions.
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Chemical Formula |
C72H60P4Pd |
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Exact Mass |
1154 |
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Molecular Weight |
1156 |
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m/z |
1154 (100.0%), 1156 (96.8%), 1153 (81.7%), 1155 (77.9%), 1157 (75.4%), 1154 (63.6%), 1158 (42.9%), 1152 (40.8%), 1159 (33.4%), 1153 (31.7%), 1156 (29.9%), 1158 (28.9%), 1155 (24.4%), 1160 (12.8%), 1154 (12.2%), 1157 (6.7%), 1159 (6.5%), 1156 (5.5%), 1150 (3.7%), 1151 (2.9%), 1161 (2.9%), 1155 (2.7%), 1158 (1.4%), 1160 (1.4%), 1157 (1.1%), 1152 (1.1%) |
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Elemental Analysis |
C, 74.84; H, 5.23; P, 10.72; Pd, 9.21 |
Tetrakis(triphenylphosphine)palladium, with the chemical formula Pd [P (C6H5) 3] 4, is an important organometallic compound with wide applications in the field of chemistry, especially in organic synthesis and catalytic reactions. The following is a detailed summary of all uses of tetratriphenylphosphine palladum:
Application in drug synthesis
Plays an important role in drug synthesis. Many drug molecules contain complex carbon carbon bonds and functional groups, which can be constructed through reactions catalyzed by the substance. For example, it has shown good catalytic activity and selectivity in the synthesis of anticancer drugs, antiviral drugs, antibacterial drugs, and other fields. In addition, it can also be used to synthesize drug intermediates, providing important raw materials and tools for drug synthesis.
Application in Materials Science
It also has a wide range of applications in materials science. It can be used as a catalyst to participate in the synthesis and modification of polymer materials, improving their performance and application range. For example, it has shown good catalytic activity and selectivity in the synthesis of conductive polymers, optical polymers, and other fields. In addition, it can also be used to synthesize new materials such as nanomaterials and inorganic organic composite materials, providing new ideas and methods for the development of materials science.
Application in Analytical Chemistry
It also has applications in analytical chemistry. For example, it can be used as an indicator for monitoring and analyzing certain chemical reactions. By observing changes in color or fluorescence properties during the reaction process, the progress and outcome of the reaction can be determined. In addition, it can also be used for the detection and separation of certain metal ions, providing importnt tools and methods for analytical chemistry.
Tetrakis(triphenylphosphine)palladium, as an important transition metal catalyst, can be used to catalyze various reactions such as coupling, oxidation, reduction, elimination, rearrangement, isomerization, etc. Its catalytic efficiency is very high, and it can catalyze many reactions that are difficult to occur under the action of similar catalysts.
Catalytic formation of carbon carbon bonds
Pd (PPh3) 4 is an important catalyst commonly used for catalyzing coupling reactions (Cross-Coupling reaction) is an important method for constructing carbon carbon bonds, characterized by mild catalytic conditions. For example, under the combined action of Pd (PPh3) 4 and Ag2O, phenylboronic acid reacts directly with aromatic halogenated hydrocarbons to produce biphenyl compounds, with a yield of 90% (Formula 1). Except for benzene
In addition to boric acid and halogenated compounds, magnesium reagents, zinc reagents, tin reagents, silicon compounds, etc. can all be used as substrates for coupling reactions.
Under the catalysis of Pd (PPh3) 4, halogenated aromatic hydrocarbons can directly react with olefin derivatives to produce styrene derivatives (this reaction type is Heck reaction) (Formula 2).
Pd (PPh3) 4 can also catalyze the coupling of alkyne compounds with halogenated compounds (Sonogashira reaction). During the reaction, alkyne hydrogen reacts with halogen elements to form hydrogen halides (or neutralizes with bases) and leaves, forming derivatives of alkynes (Formula 3).
Meanwhile, under the catalysis of Pd (PPh3) 4, the C-H bond on the aromatic ring can be activated, which can then react with halogenated compounds, tin compounds, etc. to remove one molecule of hydrogen halide or tin alkane and form C-C bond (Formula 4).
In addition, as Pd (PPh3)4 can catalyze the formation of multiple C-C bonds, it can construct reactions that catalyze multiple sites simultaneously, such as intermolecular cyclization reactions (Equation 5).
Catalytic formation of C-X bonds
Pd (PPh3) 4 can not only catalyze the synthesis of C-C bonds, but is also commonly used to construct carbon atoms and heteroatoms
Covalent bonds of N, S, O, Sn, Si, Se, P, etc. For example, many amino compounds can react under Pd (PPh3) 4 catalysis to form C-N bonds (Formula 5).
Other reactions
Some isomerization reactions commonly use Pd (PPh3) 4 as a catalyst [15,16]. Especially when the reactant molecules contain benzene rings, high yields can be obtained. For example, under the catalysis of Pd (PPh3) 4, molecules can undergo rearrangement decarboxylation reactions to generate compounds containing alkyne and alkene bonds (Formula 7).
Tetrakis(triphenylphosphine)palladium, with the chemical formula Pd [P (C6H5) 3] 4, also commonly abbreviated as Pd (PPh3) 4 or PdP4, is an important organometallic compound that plays a crucial role as a catalyst in organic synthesis. The following is a detailed introduction to its three-dimensional structure.
Its molecular structure has a high degree of symmetry. The core part is a zero valent palladum atom surrounded by four triphenylphosphine (PPh3) ligands. These four P atoms are arranged in a tetrahedral geometry around the palladum atom, forming a four coordinate complex that conforms to the 18 electron rule. This structure places palladum atoms at the tetrahedral center formed by four equidistant P atoms, ensuring the stability and reactivity of the molecule.
Each triphenylphosphine ligand is an organic compound containing phosphorus, with one phosphorus atom and three benzene rings. Phosphorus atoms are connected to palladum atoms through covalent bonds, while benzene rings are connected to phosphorus atoms through sigma bonds. This structure endows triphenylphosphine ligands with significant steric hindrance and good electronic effects, which helps stabilize palladum complexes and affect their activity in chemical reactions.
Although the basic structure is a regular tetrahedron, the compound may exhibit some stereoisomerism in solution due to steric hindrance and electronic effects between ligands. This heterogeneity mainly comes from the relative orientation and arrangement of ligands around palladum atoms. However, this heterogeneity usually has a relatively small impact on the catalytic activity of compounds, as palladum atoms are always in the central position of tetrahedra, and the electronic effects and steric hindrance of the four ligands are relatively balanced.
In solution, one or more triphenylphosphine ligands can be reversibly dissociated to form low coordination complexes such as Pd (PPh3) 3 or Pd (PPh3) 2. These low coordination complexes typically exhibit higher activity in chemical reactions because they are more likely to interact with substrates. In addition, catalytic reactions can also undergo processes such as oxidation addition and reduction elimination to achieve catalytic cycling.
Tetrakis (triphenylphosphine) palladium, abbreviated as Pd (PPh3) ₄, is one of the most important transition metal complexes in modern organic chemistry, widely used in catalytic processes such as cross coupling reactions, hydrogenation reactions, and carbon heteroatom bond formation. In 1893, Swiss chemist Alfred Werner proposed the coordination theory, which for the first time systematically elucidated the nature of coordination bonds between metal centers and ligands, laying the theoretical foundation for transition metal complex chemistry. Werner's work explains why certain metals (such as Co, Pt, Pd) can form stable complexes with multiple neutral or anionic ligands. In the early 20th century, research on the chemical properties of palladium (Pd) lagged behind that of platinum (Pt). In the 1930s, Soviet chemist Ilya Chernyaev systematically studied the planar quadrilateral complexes of Pd (II) and found that the complexes formed with amines and halide ions exhibited unique stability. In 1948, British chemist Joseph Chatt first reported the existence of Pd (0) complexes, but was unable to isolate pure samples at that time. In the late 1950s, Geoffrey Wilkinson's team at Imperial College London (winner of the 1973 Nobel Prize in Chemistry) developed triphenylphosphine (PPh3) as a universal ligand and discovered its ability to form stable complexes with various transition metals. In 1961, Wilkinson successfully synthesized Rh (PPh ∝) ∝ Cl (Wilkinson catalyst), greatly promoting the development of phosphine ligand chemistry.
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