19232-05-4

Usage

Uses

Used in Organic Synthesis:
Dichlorobis(trimethylphosphine)nickel(II) is used as a catalyst for several applications in the field of organic synthesis, including:
1. Wenkert arylation of thiophene with aryl Grignard reagents: This catalyst enables the selective arylation of thiophene, a key step in the synthesis of various biologically active compounds and pharmaceuticals.
2. Regioselective [2+2+2] cycloaddition of carboryne with alkynes to give benzocarborane compounds: This reaction is important for the synthesis of complex organic molecules, particularly those with potential applications in materials science and pharmaceuticals.
3. Kumada-Corriu cross coupling of Grignard reagents: This catalyst facilitates the cross coupling of Grignard reagents, a widely used method for the formation of carbon-carbon bonds in organic synthesis.
4. Borylation of aryl chlorides: This reaction allows for the selective borylation of aryl chlorides, which is crucial for the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
5. Reductive aldol cyclization-lactonization: This catalyst enables the reductive aldol cyclization-lactonization reaction, which is a key step in the synthesis of complex organic molecules, particularly those with potential applications in the pharmaceutical industry.
6. Arylcyanation of alkynes: This reaction is important for the synthesis of various organic compounds, including those with potential applications in the fields of materials science and pharmaceuticals.
7. Alkynylation of benzonitriles via C-C bond activation: This catalyst facilitates the alkynylation of benzonitriles, a key step in the synthesis of various organic compounds, particularly those with potential applications in the pharmaceutical and agrochemical industries.

InChI:InChI=1/2C3H9P.2ClH.Ni/c2*1-4(2)3;;;/h2*1-3H3;2*1H;/q;;;;+2/p-2

Upstream product

• 83864-14-6 nickel dichloride 
• 594-09-2 trimethylphosphane 
• 29046-78-4 (1,2-dimethoxyethane)dichloronickel(II) 

Downstream Products

• 89453-50-9 trans-Ni(C₆H₄Me-2)2(PMe₃)2 
• 85096-37-3 C₃₆H₃₀N₂NiP₂ 
• 203192-36-3 Ni(II)Cl(P(CH₃)3) (o-diphenylphosphino)-N-(trimethylphosphoranyl)phenylimine 
• 529496-90-0 chloro[2-(diphenylphosphanyl)-N-(trimethylsilyl)anilido-N,P](trimethylphosphane)nickel(II) 
• 529496-88-6 chloro[2-(diphenylphosphanyl)anilido-N,P](trimethylphosphane)nickel(II) 
• 7440-02-0 nickel 

Relevant academic research and scientific papers

Evaluating a Dispersion of Sodium in Sodium Chloride for the Synthesis of Low-Valent Nickel Complexes**

The use of a sodium in sodium chloride dispersion is systematically evaluated for the synthesis of nickel(0) and nickel(I) complexes from readily-prepared nickel(II) precursors. A variety of complexes with phosphine and bipyridine-type ligands were accessed, although some reactions were found to produce mixtures of nickel(0) and nickel(I), and yields were highly variable. Several new nickel(I) complexes were obtained, and these were characterized using techniques including NMR spectroscopy, EPR spectroscopy, and single crystal X-ray diffraction analysis.

Bridged and Unbridged Nickel-Nickel Bonds Supported by Cyclopentadienyl and Phosphine Ligand Sets

A series of Ni complexes [Ni(Cl)2(PR3)2] with R = Me (1-Me), nPr (1-nPr), and nBu (1-nBu) and nickelocenes [Ni(η5-C5H4R′)2] with R′ = H (2-H), Me (2-Me), and SiMe3 (2-SiMe3) were synthesized and characterized. From these complexes, the synthesis of the Ni complexes [NiCl(PR3)(η5-C5H4R′)] R = Me, R′ = H (3-Me), R= nBu, R′ = H (3-nBu), R = nPr, R′ = H (3-nPr), R = Et, R′ = Me (4), and R = Et, R′ = SiMe3 (5) was achieved. All complexes were fully characterized, including single crystal X-ray crystallography. Complexes 3-R, 4, and 5 were then used to obtain homobimetallic Ni complexes with rare examples of unbridged Ni-Ni bonds [{Ni(η5-C5H5)(PR3)}2], with R = Me (7-Me) and R = nPr (7-nPr) being structurally characterized by single crystal X-ray diffraction. In order to probe the effect of bridging ligands on the Ni-Ni bond, the bridged complex [{Ni(μ:η5-C5H4CH2CH2P(tBu)2)}2] (8) was synthesized from the monomeric precursor [Ni(Cl)(κ1-η5-C5H4CH2CH2PtBu2)] (6). The Ni-Ni distances in 7-Me, 7-nPr, and 8 were found to be 2.407(1), 2.3931(6), and 2.6027(17) ?, respectively, the latter seemingly lengthened compared to the other two due to the tethered nature of the bridging ligand. DFT calculations confirm the presence of unbridged σ-bonds between the Ni atoms in 7-Me and 7-nPr and show that the bridging ligand in 8 has a minimal effect on the character of the Ni-Ni bond.