25136-46-3

Usage

Uses

Used in Organic Synthesis:
Tris(triphenylphosphine)nickel(0) is used as a catalyst for cross-coupling reactions in organic synthesis. It plays a crucial role in facilitating carbon-carbon bond formation, making it an essential component in the synthesis of complex organic molecules.
Used in the Heck Reaction:
In the field of organic chemistry, Tris(triphenylphosphine)nickel(0) is used as a catalyst in the Heck reaction, a type of cross-coupling reaction that involves the coupling of an alkene with an aryl or vinyl halide in the presence of a base. This reaction is widely used for the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Used in the Suzuki Reaction:
Tris(triphenylphosphine)nickel(0) is also employed as a catalyst in the Suzuki reaction, another cross-coupling reaction that involves the coupling of an aryl or vinyl boronic acid with an aryl or vinyl halide. This reaction is particularly useful for the formation of biaryl compounds, which are common structural motifs in pharmaceuticals, agrochemicals, and materials science.
Used in the Stille Reaction:
In the Stille reaction, Tris(triphenylphosphine)nickel(0) serves as a catalyst for the cross-coupling of an organotin compound with an aryl or vinyl halide. This reaction is widely used for the synthesis of conjugated organic materials, such as polymers and oligomers, which have applications in electronic devices and optoelectronics.
Used in the Pharmaceutical Industry:
Tris(triphenylphosphine)nickel(0) is used as a catalyst in the synthesis of various pharmaceutical compounds, where its ability to facilitate carbon-carbon bond formation is crucial for the production of complex drug molecules.
Used in the Agrochemical Industry:
In the agrochemical industry, Tris(triphenylphosphine)nickel(0) is employed as a catalyst for the synthesis of agrochemical compounds, such as pesticides and herbicides, where its cross-coupling capabilities are essential for the creation of novel and effective molecules.
Used in Materials Science:
Tris(triphenylphosphine)nickel(0) is utilized as a catalyst in the synthesis of conjugated organic materials for applications in materials science, including the development of new polymers, oligomers, and other materials with potential use in electronic devices and optoelectronics.

Upstream product

• 23777-40-4 bis(triphenylphosphine)ethylenenickel⁽⁰⁾ 
• 172294-41-6 (η(2)-C6H8)Ni(PPh3)2 
• 1295-35-8 bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ 
• 127965-92-8 ((C₂H₅)2N)3TiP(C₆H₁₁)2 
• 36673-36-6 dibromobis(triphenylphosphine)nickel(II) 
• 55091-64-0 1-methyl-1-phenyl-2-bromocyclopropane 
• 754-05-2 ethenyltrimethylsilane 
• 49676-92-8 1,2-dibromocyclohex-1-ene 
• 603-35-0 triphenylphosphine 
• 83864-14-6 nickel dichloride 
• 14264-16-5 bis(triphenylphosphine)nickel(II) chloride 
• 74-85-1 ethene 

Downstream Products

• 23777-40-4 bis(triphenylphosphine)ethylenenickel⁽⁰⁾ 
• 15376-83-7 (triphenylphosphine)3(CO)nickelk 
• 89606-46-2 (η2-methylenecyclopropane)bis(triphenylphosphine)nickel 
• 117111-20-3 (η2-1,3,3-trimethylcyclopropene)bis(triphenylphosphine)nickel 
• 117111-19-0 (η2-2,2-dimethyl-1-methylenecyclopropane)bis(triphenylphosphine)nickel 
• 125645-45-6 (η2-tetramethylcyclopropene)bis(triphenylphosphine)nickel 
• 15169-65-0 tris(triphenylphosphine)nickel(I) iodide 
• 603-35-0 triphenylphosphine 
• 96095-76-0 Ni(P(C₆H₅)3)2(CH₂C(C(CH₃)2)C(C(CH₃)2)CH₂) 
• 51351-78-1 C₅H₈Ni(P(C₆H₅)3)2 
• 13007-90-4 Ni(CO)2(P(C₆H₅)3)3 

Relevant academic research and scientific papers

Synthesis of controlled π-extended conjugate nanostructures of 1,1′-ferrocene

Synthesis of the (E,E)-1,1′-ferrocene nanostructures having controlled π-extended conjugation was satisfactory carried out starting of 1′-[2-(1,3-dioxolan)]-1-formylferrocene (1). The molecular unit (E)-1′-[2-(1,3-dioxolan)]-1-[β-(p-iodophenyl)ethenyl]ferrocene (2), was obtained in excellent yield by treatment of 1 with p-iodobenzyl triphenylphosphonium ylid followed by Z→E isomerization, catalyzed by iodine, in quantitative yield. Compound (E)-2 was transformed in (E)-1′-{2-(1,3-dioxolan)-1-[β-[4-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl]-ethenyl}ferrocene, (E)-4, by palladium catalyzed cross-coupling with 2-methyl-but-3-yn-2-ol. (E)-4 gives (E)-1-[β-(4-ethynylphenyl)-ethenyl]-1′-[2-(1,3-dioxolan)]ferrocene (E)-5 by powder sodium hydroxide treatment. The molecular unit (E,E)-1-{β-[4-(β-(1′-formylferrocenyl)-ethenyl)-phenylethynyl]-phenyl]-ethenyl}-1′-formylferrocene, (E,E)-6, was synthesized by palladium catalyzed cross-coupling between the p-iodophenyl derivative (E)-2 and their ethynyl derivative (E)-5, in good yield. The (E,E)-1,1′-(p-iodophenyl)ethenyl ferrocene, (E,E)-7, was synthesized by reaction between 1,1′-diformylferrocene and the p-iodobenzyltriphenylphosphonium ylid, as a mixture of isomers which were purely isolated. Moreover, isomerization of the Z,Z and E,Z mixture to the E,E isomer, was induced by sunlight exposure, catalyzed by iodine, in quantitative yield. The (E,E)-1,1′-[β-(4-ethynylphenyl)-ethenyl]ferrocene, (E,E)-10, was synthesized in good yield, by palladium catalyzed cross-coupling of compound (E,E)-7 with 2-methyl-but-3-yn-2-ol, followed by powder sodium hydroxide treatment.

The crystal and molecular structure of the coordinatively unsaturated Ni(0) species Ni(PPh3)3

The disproportionation of the complex (Et2N)3Ti(μ-PCy2)Ni(PPh3) affords the coordinatively unsaturated species Ni(PPh3)3, 1. This compound crystallizes in the triclinic space group PI, with a = 18.483(4) ?, b = 16.203(3) ?, c = 17.783(4) ?, a = 105.85(2)°, β = 117.33(3)°, γ = 92.33(3)°, Z = 4, and V = 4464(2) ?3. Full-matrix least-squares refinement of 1042 variables using 6484 data (F02 > 3crF02) gave R = 0.0441 and Rw = 0.0438. The two crystallographically independent molecules are essentially identical, each exhibiting a trigonal planar coordination sphere at Ni. The most interesting feature of the structure is the close approach (2.744-3.094 ?) of three ortho hydrogens of the PPh3 groups to the Ni centres. The implications of the structural data regarding ortho metallation and the known instability of 1 are discussed.

Quaternary aryl phosphonium salts as corrosion inhibitors for iron in HCl

Cathodic and anodic Tafel extrapolation data for the corrosion inhibition of iron in deaerated 1 M HCl at 22 °C are obtained for five synthesized phosphonium salts, 4-tolyltriphenyl-phosphonium chloride (TTPPC), 4-phenoltriphenylphosphonium chloride (PTPP

Synthesis and reactions of nickel(0) η2-cyclohexyne complexes and X-ray crystal structure of Ni(η2-C6H8)(C6H 11)2PCH2CH2P(C6H 11)2

Reduction of 1,2-dibromocyclohexene with 1% sodium amalgam in the presence of Ni(η2-C2H4)L2 gives cyclohexyne nickel(O) complexes Ni(η2-C6H8)L2 [L2 = 2PPh3 (1), dcpe (2), 2PEt3 (3); dcpe = 1,2-bis(dicyclohexylphosphino)ethane, Cy2PCH2CH2PCy2], which are structurally similar to, but less stable than, the corresponding platinum(O) compounds. The crystal structure of 2 has been determined. The molecule contains a nickel atom bound to η2-cyclohexyne [Ni-C(1) = 1.875(4) A?, Ni-C(2) = 1.867(4) A?] and to dcpe [Ni-P(1) = 2.139-(1) A?, Ni-P(2) = 2.138(1) A?]. The geometry is close to trigonal planar if the midpoint of the coordinated triple bond is regarded as occupying one coordination site, and the C=C distance [1.272(5) A?] is slightly less than that in Pt(η2-C6H8)(PPh3)2 [1.297(8) A?]. Complex 2 reacts with methyl iodide and with CO2 to give insertion products containing nickel(II), NiI(2-MeC6H8)(dcpe) (7) and Ni{C6H8C(O)O}(dcpe)(9), respectively. Dimethyl acetylenedicarboxylate inserts into the Ni-C σ-bond of 9 to give a seven-membered nickelacycle Ni{C(CO2-Me)=C(CO2Me)C6H 8C(O)C-(dcpe) (10).

On the interaction of a nickel(0) complex with mono- and di-bromo derivatives of cyclopropane. Novel η3-allylnickel complexes

The interaction of (η2-ethylene)bis(triphenylphosphine)nickel(0) with 1-bromo-2-methyl-2-phenyl- and 1,1,-dibromo-2-methyl-2-phenyl-cyclopropane has been studied.These reactions were expected to proceed with opening of the three-membered ring a

The crystal and molecular structure of the coordinatively unsaturated Ni(0) species Ni(PPh3)3

The disproportionation of the complex (Et2N)3Ti(μ-PCy2)Ni(PPh3) affords the coordinatively unsaturated species Ni(PPh3)3, 1.This compound crystallizes in the triclinic space group P1, with a = 18.483(4) Angstroem, b = 16.203(3) Angstroem, c = 17.783(4) Angstroem, α = 105.85(2) deg, β = 117.33(3) deg, γ = 92.33(3) deg, Z = 4, and V = 4464(2) Angstroem3.Full-matrix least-squares refinement of 1042 variables using 6484 data (F02 > 3?F02) gave R = 0.0441 and Rw = 0.0438.The two crystallographically independent molecules are essentially identical, each exhibiting a trigonal planar coordination sphere at Ni.The most interesting feature of the structure is the close approach (2.744 - 3.094 Angstroem) of three ortho hydrogens of the PPh3 groups to the Ni centres.The implications of the structural data regarding ortho metallation and the known instability of 1 are discussed.

Mechanistic study of the reactions of 1,1-dimethylallene with nickel(O) complexes. π- and σ-complex formation vs. electron transfer

The reactions of 1,1-dimethylallene (DMA) with several Ni(0) complexes have been studied. Kinetic and NMR studies on the reaction of DMA with tris(triphenylphosphine)nickel(0) [(TPP)3Ni] indicate the formation of mono(1,1-dimethylallene)-, cis- and trans-bis(1,1-dimethylallene)-, and tris(1,1-dimethylallene)nickel complexes, the ratio of the complexes depending on the concentration of DMA and added TPP. At temperatures below -60°C the cis-bis(DMA) π-complex [and possibly the tris(DMA) π-complex] undergoes coupling to form mainly the 3,4-bis(isopropylidene)nickelacyclopentane complex 30. At temperatures above -15°C, 30 undergoes hydrogen atom migration and reductive elimination to form 12. The reaction of tris(triethylphosphine)nickel(0) with DMA also results in the formation of 12; however, the extent of mono-, bis-, and tris(DMA) π-complex formation is much less. In contrast, DMA reacts with (COD)2Ni in an electron-transfer process to initially form the DMA radical anion. The overall reaction is very complex. Carbonylation of the finally derived complex(es) produces the two isomeric, trimeric ketones 22 and 24. The reaction of DMA with the mixed-ligand complexes (cyclooctadiene)(triphenylphosphine)nickel(O) and (cyclooctadiene)(ethyl acrylate)nirkel(0) proceed in a manner similar to that with the substituted-phosphine complexes.

NICKEL COMPLEXES WITH VINYLSILANES

Three methods for preparing the following nickel complexes of vinylsilanes are described: (CH2=CHSiR3)Ni(PPh3)2 (R = Me, OMe), Ni(PPh3)2, 2, Ni(PPh3), Ni(PPh3) and Ni(PPh3)