Tetrakis(triphenylphosphine)palladium

Base Information

• Chemical Name: Tetrakis(triphenylphosphine)palladium
• CAS No.: 14221-01-3
• Deprecated CAS: 12582-12-6,136296-64-5,136296-64-5
• Molecular Formula: C72H60P4Pd
• Molecular Weight: 1155.58
• Hs Code.: 28439090
• European Community (EC) Number: 238-086-9
• DSSTox Substance ID: DTXSID9065732
• Nikkaji Number: J3.371.367C
• Wikipedia: Tetrakis(triphenylphosphine)palladium(0)
• Wikidata: Q2366402
• Mol file: 14221-01-3.mol

Synonyms:14221-01-3;Tetrakis(triphenylphosphine)palladium;Tetrakis(triphenylphosphine)palladium(0);Tetrakis(triphenylphosphine) palladium(0);Tetra(triphenylphosphine)palladium;palladium;triphenylphosphane;Palladium-tetrakis(triphenylphosphine);PD(PPH3)4;UNII-N9O1RWZ93J;Palladium, tetrakis(triphenylphosphine)-, (T-4)-;Palladium (0) tetrakis(triphenylphosphine);EINECS 238-086-9;tetrakis(triphenylphosphane) palladium;Pd(P(C6H5)3)4;Pd[P(C6H5)3]4;N9O1RWZ93J;palladium tetrakis(triphenylphosphine);Palladium tetrakis[triphenylphosphine];tetrakis(triphenylphosphine) palladium;tetrakis[triphenylphosphine] palladium;tetrakis [triphenylphosphine] palladium;tetrakis(triphenyl-phosphine) palladium;tetrakis[triphenyl-phosphine] palladium;Tetrakis (triphenylphosphine) palladium;tetrakis[triphenylphosphine]palladium(0);tetrakis(triphenylphosphine)-palladium(0);tetrakis[triphenylphosphine]-palladium(0);tetrakis (triphenylphosphine)-palladium(0);tetrakis [triphenylphosphine]-palladium(0);Tetrakis(triphenylphosphine) palladium (0);MFCD00010012;tetrakis;tetrakis(triphenylphosphine)palladium(o);palladiumtetrakis;Pd tetrakis;Pd-tetrakis;PALLADIUM TETRAKIS-(TRIPHENYLPHOSPHINE);palladium-tetrakis;Palladium tetrakis;(Ph3P)4Pd;(PPh3)4Pd;Pd(Ph3P)4;TETRAKIS(TRIPHENYL PHOSPHINE) PALLADIUM;(Ph3P)4 Pd;(PPh3)4 Pd;Pd (PPh3)4;tetrakistriphenylphosphine Pd;C72H60P4Pd;triphenylphosphonium;tetrakistriphenylphoshine Pd(0);DTXSID9065732;tetrakistriphenylphosphine Pd(0);C72-H60-P4-Pd;tetrakistriphenylphosphinepalladium;NFHFRUOZVGFOOS-UHFFFAOYSA-N;tetrakistriphenyl phosphine Pd(0);XLTFHSIALNLSTH-UHFFFAOYSA-N;Palladium tetra(triphenylphosphine);tetra(triphenylphosphine) palladium;tetrakistriphenyl-phosphinepalladium;tetrakistriphenylphosphine-palladium;terakis(triphenylphosphine)palladium;tetrakistriphenyl phosphine Pd (0);AMY39328;palladium tetra(triphenyl phosphine);palladiumtetrakis(triphenylphosphine);STR01746;Palladium terakis(triphenylphosphine);tetrakis(triphenylphosphin)-palladium;tetrakistriphenylphospinepalladium(0);AC-782;BBL100058;STL511030;palladiumtetrakis(triphenyl phosphine);tetra kis (triphenylphospine)palladium;tetra-kis(triphenylphosphine)palladium;tetrakis(triphenylphosphine)-palladium;tetrakis-(triphenylphosphin)-palladium;tetrakistriphenylphosphinepalladium(0);AKOS005259864;palladium - 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Chemical Property of Tetrakis(triphenylphosphine)palladium

Chemical Property:

• Appearance/Colour: yellow crystals
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 103-107 ºC
• Boiling Point: 360oC at 760 mmHg
• Flash Point: 181.7oC
• PSA: 54.36000
• LogP: 13.77920
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive/Air Sensitive
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 12
• Exact Mass: 1154.26803
• Heavy Atom Count: 77
• Complexity: 202

Purity/Quality:

99% ^*data from raw suppliers

Tetrakis(triphenylphosphine)palladium(0) 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 20/22-40-36/37/38
• Safety Statements: 22-24/25-36/37-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Organic Compounds, Metal Salts
• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd]
• Uses: suzuki reaction Tetrakis(triphenylphosphine)palladium(0) is widely used as a catalyst for palladium-catalyzed coupling reactions. Pd(PPh3)4 is widely used as a catalyst for palladium-catalyzed coupling reactions. Prominent applications include the Heck reaction, Suzuki coupling, Stille coupling, Sonogashira coupling, and Negishi coupling. A high-yielding catalyst used in coupling reactions.

Technology Process of Tetrakis(triphenylphosphine)palladium

There total 127 articles about Tetrakis(triphenylphosphine)palladium which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

palladium tetraammine di(hydrogen carbonate) + triphenylphosphine (603-35-0) → tetrakis(triphenylphosphine) palladium(0) (14221-01-3)

Guidance literature:

In methanol; for 1.5h; Heating / reflux;

Reference yield: 97.6%

triphenylphosphine (603-35-0) + palladium dichloride → tetrakis(triphenylphosphine) palladium(0) (14221-01-3)

Guidance literature:

With sodium hydrogencarbonate; ascorbic acid; In dimethyl sulfoxide; at 20 - 60 ℃; for 2.33333h; Reagent/catalyst;

Reference yield: 95.0%

palladium dichloride → tetrakis(triphenylphosphine) palladium(0) (14221-01-3)

Guidance literature:

With triphenylphosphine; hydrazine; In water; N,N-dimethyl-formamide; N2; refluxing PdCl2 and PPh3 (30 min), addn. of aq. N2H4 (80°C); pptn., filtration, washing (MeOH, ether), drying;

DOI:10.1016/0022-328X(85)87317-4

upstream raw materials:

palladium diacetate

triphenylphosphine

palladium diacetate

tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex

Downstream raw materials:

methyl 5-chloro-2-cyanobenzoate

anilazine

benzyl N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-fluorophenyl]carbamate

2-ethyl-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-3-nitro-pyridine

Refernces

Suzuki reaction on pyridinium N-(5-bromoheteroar-2-yl)aminides

10.1016/j.tetlet.2004.09.136

The study focuses on the reactivity of substituted pyridinium N-(20-azinyl)aminides in the Suzuki–Miyaura cross-coupling reaction, a widely used method for forming sp2–sp2 carbon–carbon bonds. The researchers investigated the coupling of these compounds with various boronic acids, using Cs2CO3 as a base, which resulted in good yields and substitution on the negatively charged moiety. They optimized the reaction conditions and found that the process was efficient for a range of substrates, including those with electron-deficient diazine rings, albeit requiring longer reaction times. The study also explored a double Suzuki process with a dibromoaminide to yield diarylated ylides. The results provide a valuable strategy for the synthesis of functionalized 2-aminoazines, which are important in medicinal and heterocyclic chemistry, and the researchers are continuing their efforts to expand the application of this process to other N-aminides.

Generation of a small library of highly electron-rich 2-(hetero)aryl- substituted phenethylamines by the Suzuki-Miyaura reaction: A short synthesis of an apogalanthamine analogue

10.1002/ejoc.200400213

The research focuses on the synthesis of a small library of highly electron-rich 2-aryl and 2-heteroaryl phenethylamines (PEAs) using the Suzuki-Miyaura cross-coupling reaction, which is enhanced by microwave irradiation for improved reaction yield and speed. The study commenced with the synthesis of benzyl [2-(2-bromo-4,5-dimethoxyphenyl)ethyl]carbamate from 2-(3,4-dimethoxyphenyl)ethylamine, followed by its coupling with various boronic acids to generate the PEAs. The reactions were optimized using sodium hydrogencarbonate as the base and tetrakis(triphenylphosphane)palladium(0) as the catalyst, with the mixture of N,N-dimethylformamide and water as the solvent. The synthesized compounds were characterized by 1H and 13C NMR spectroscopy, and low-resolution mass spectrometry (LR-MS) to confirm their structures and purities. The research also successfully extended this methodology to synthesize an apogalanthamine analogue, a complex natural product with significant biological activities, showcasing the versatility and efficacy of the developed synthetic strategy.

Control of regioselectivity in Pd(0)-catalyzed coupling-cyclization reaction of 2-(2′,3′-allenyl)malonates with organic halides

10.1021/jo0108616

The research focuses on controlling the regioselectivity in Pd(0)-catalyzed coupling-cyclization reactions of 2-(2′,3′-allenyl)malonates with organic halides. The study explores how steric and electronic effects of the substrates influence the regioselectivity, and through the manipulation of reaction conditions, the researchers can tune the reaction to afford either vinylic cyclopropane derivatives or cyclopentene derivatives selectively. The experiments involved the use of different solvents, bases and substrates, with Pd(PPh3)4 (Tetrakis(triphenylphosphine)palladium(0)) as the catalysts to form the desired products with high selectivity. Analytical techniques such as infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (1H NMR), and mass spectrometry (MS) are employed to characterize the reactants and products, with detailed spectral data provided for each new compound synthesized. The research also includes the preparation of various 2,3-allenic acid esters and 2,3-allen-1-ols, which are used as starting materials in the Pd(0)-catalyzed reactions.

Synthesis of sulfur heterocycles via domino metal-mediated reactions

10.1080/10426507.2016.1255621

The research focuses on the development of two methodologies for synthesizing sulfur heterocycles (S-heterocycles) and mixed nitrogen-sulfur heterocycles (N,S-heterocycles) through metal-mediated domino reactions. The first methodology involves a cyclocarbopalladation/cross-coupling domino process, utilizing propargyl sulfides or ynethioethers as starting materials and Pd(PPh3)4 as a catalyst, with Stille or Suzuki-Miyaura coupling partners like 2-furyl, 2-thienyl, allyl, and vinyl tributylstannanes, or arylboronic acids. This approach yields benzene-fused five- or six-membered sulfur heterocycles with a stereodefined tetrasubstituted exocyclic double bond. The second methodology is a three-component domino reaction between 2-aminophenyl disulfide, copper cyanide (CuCN), and an electrophile, which accesses N-substituted 2-amino benzothiazoles. The experiments also explore the synthesis of N-substituted 2-imino benzothiazoles using N-protected 2-aminoaryl disulfides as precursors. The analyses used to confirm the structures of the synthesized compounds include X-ray crystallography, with crystallographic data deposited at the Cambridge Crystallographic Data Center.

Novel synthesis of hexaaryl[3]radialenes via dibromo[3]dendralenes

10.1016/S0040-4039(00)01211-9

The research focuses on the novel synthesis of highly fluorescent hexaaryl[3]radialenes, which are compounds of interest due to their electron-rich nature and potential use in electron donor and acceptor systems. The synthesis involves the oligomerization of ate-type copper carbenoids, followed by cyclization with hexamethylditin and Pd(PPh3)4. The structures of the intermediate [3]dendralene and the final hexaaryl[3]radialenes were confirmed through X-ray crystallographic analysis. The experiments utilized reactants such as ate-type copper carbenoids, hexamethylditin, and Pd(PPh3)4, and employed various analytical techniques including NMR, UV spectroscopy, and cyclic voltammetry to characterize the compounds and measure their redox properties. The study also examined the fluorescence properties of the synthesized radialenes, finding that the introduction of a chlorine atom in compound 4 enhanced its fluorescence quantum yield compared to compound 3.

Palladium-catalyzed silylation reaction between benzylic halides and silylboronate

10.1039/c6cc00713a

The study presents an efficient palladium-catalyzed silylation reaction between benzylic halides and silyboronate, which allows for the synthesis of benzylic silanes. The reaction accommodates a broad substrate scope and proceeds under mild conditions, yielding products with moderate to high yields and stereospecificity. Key chemicals used include primary and secondary benzylic halides, silyboronates, and palladium catalysts such as Pd(PPh3)4, along with silver oxide (Ag2O) as a co-catalyst. These chemicals serve the purpose of facilitating the formation of C-Si bonds, which are important in the synthesis of bioactive molecules and organic materials. The study also explores the reaction's mechanism and demonstrates that it can be used for the synthesis of various benzyl silane compounds, including those with sensitive functional groups, and maintains enantiopurity in enantioenriched substrates.

Palladium-catalyzed α-ketocyclopropanation of norbornenes with propargyl acetates

10.1021/jo500357f

The research describes a palladium-catalyzed α-ketocyclopropanation reaction of norbornenes with propargyl acetates, which is a method for the synthesis of cyclopropyl ketones with high stereoselectivity. The purpose of the study was to develop a [2 + 1] cycloaddition reaction that does not require an oxygen substituent at the center carbon, diverging from the typical precursors used in such reactions. The researchers found that using tetrakis(triphenylphosphine)palladium as a catalyst, they could achieve moderate to good yields of the corresponding cyclopropanes from various substituted norbornenes. Key chemicals used in the process include norbornene derivatives, propargyl acetates, and the palladium catalyst. The reaction was sensitive to the choice of solvent and the presence of water, with acetonitrile being the optimal solvent and a certain amount of water enhancing the reaction yield. The study concluded that the oxygen atom in the resulting cyclopropyl ketones likely originates from residual water in the acetonitrile or reagents, rather than from external oxygen sources. The reaction mechanism was also proposed, involving the formation of an allenylpalladium intermediate and subsequent steps leading to the final product.

Reaction of Arylazo Aryl Sulfone with Olefins in the Presence of Tetrakis(triphenylphosphine)palladium(0)

10.1246/cl.1987.347

The research investigates the catalytic reaction of arylazo aryl sulfones with olefins in the presence of tetrakis(triphenylphosphine)palladium(0). The primary purpose is to explore the arylation of olefins using arylazo aryl sulfones as versatile precursors for various reactive species. Key chemicals used include arylazo aryl sulfones such as phenylazo p-tolyl sulfone, styrene as the olefin, and tetrakis(triphenylphosphine)palladium(0) as the catalyst. The study concludes that arylated olefins are the major products, with a 1:1 adduct of arylazo and arenesulfonyl groups to olefins as a minor product. The formation of diarylpalladium(II) species is proposed as an intermediate in the reaction mechanism. The results suggest that the reaction proceeds via oxidative addition of the arylazo aryl sulfone to the palladium(0) catalyst, followed by reductive elimination to regenerate Pd(0) and produce the arylated products. The study also highlights the potential for further exploration of the scope and limitations of this reaction.

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