94202-32-1

Upstream product

• 12150-46-8 1,1'-bis-(diphenylphosphino)ferrocene 
• 67292-34-6 [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride 
• 1295-35-8 bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ 
• 1427853-67-5 (1,1′-bis(diphenylphosphino)ferrocene)Ni(η²-ethylene) 
• 5980-97-2 mesitylboronic acid 
• 100379-00-8 2,6-dimethylbenzene boronic acid 

Downstream Products

• 102-54-5 ferrocene 

Relevant academic research and scientific papers

Nickel(I) Aryl Species: Synthesis, Properties, and Catalytic Activity

In this work, Ni(I) aryl species that are directly relevant to cross-coupling have been synthesized. Transmetalation of (dppf)NiIX (dppf = 1,1′-bis(diphenylphosphino)-ferrocene, X = Cl, Br) with aryl Grignard reagents or aryl boronic acids in t

Low-valent nickel and palladium complexes with 1,1′-bis(phosphanyl)- ferrocenes: Syntheses and structures of acrylic acid and ethylene complexes

Thermally stable acrylic acid complexes with low-valent nickel or palladium of the type [(L)M(η2-CH2=CH-COOH)] [1a: M = Ni, L = 1,1′-bis(diphenylphosphanyl)ferrocene (dppf), 1b: M = Ni, L = 1,1′-bis(diisopropylphosphanyl)ferrocene (d

Comparison of dppf-Supported Nickel Precatalysts for the Suzuki-Miyaura Reaction: The Observation and Activity of Nickel(I)

Ni-based precatalysts for the Suzuki-Miyaura reaction have potential chemical and economic advantages compared to commonly used Pd systems. Here, we compare Ni precatalysts for the Suzuki-Miyaura reaction supported by the dppf ligand in 3 oxidation states, 0, I and II. Surprisingly, at 80 °C they give similar catalytic activity, with all systems generating significant amounts of NiI during the reaction. At room temperature a readily accessible bench-stable NiII precatalyst is highly active and can couple synthetically important heterocyclic substrates. Our work conclusively establishes that NiI species are relevant in reactions typically proposed to involve exclusively Ni0 and NiII complexes.

Stable nickel(0) phosphites as catalysts for C-N cross-coupling reactions

Herein we describe the design and preparation of inexpensive, air-stable nickel phosphite-based catalysts for use in the C-N cross-coupling reaction. The combination of nickel tetrakis(triphenyl phosphite) {Ni[P(OPh) 3]4} and 1,1'-bis(diphenylphosphino)ferrocene (dppf), and in particular a newly developed catalyst (dppf)Ni[P(OPh)3] 2, were found to be extremely effective in catalyzing a range of amination reactions of anilines and amines with aryl chlorides. This new catalyst system offers an alternative to the bis(cyclooctadienyl)nickel [Ni(COD)2] and palladium(0) catalysts commonly used for C-N bond formation.

Lewis acid induced β-elimination from a nickelalactone: Efforts toward acrylate production from CO2 and ethylene

The Lewis acid tris(pentafluorophenyl)borane was found to rapidly promote ring-opening β-hydride elimination in a 1,1′-bis(diphenylphosphino) ferrocene (dppf) nickelalactone complex under ambient conditions. The thermodynamic product of nickelalactone ring-opening was characterized as (dppf)Ni(CH(CH3)CO2BArf3), the result of β-hydride elimination and subsequent 2,1-insertion from a transient nickel(II) acrylate hydride intermediate. Treatment of (dppf)Ni(CH(CH3)CO2BArf3) with a nitrogen-containing base afforded a diphosphine nickel(0) η2- acryl borate adduct. Formation of the diphosphine nickel(0) η2- acryl borate adduct completes a net conversion of nickelalactone to acrylate species, a significant obstacle to catalytic acrylate production from CO 2 and ethylene. Displacement of the η2-acrylate fragment from the nickel center was accomplished by addition of ethylene to yield a free acrylate salt and (dppf)Ni(CH2CH2).

Homoleptic complexes of cobalt(0) and nickel(0,I) with 1,1′- bis(diphenylphosphino)ferrocene (dppf): Synthesis and characterization

Reduction of Co(dppf)Cl2 with 2 equiv of sodium naphthalenide in THF, in the presence of dppf, affords the homoleptic complex Co(dppf) 2, 1, isolated in 65% yield as a brick red solid, extremely air sensitive. In solution, under inert atmosphere, 1 slowly decomposes into Co and dppf, following a first-order kinetic law (t1/2 = 21 h at 22°C). Similarly to the Rh and Ir congeners, 1 undergoes a one-electron reversible reduction to [Co(dppf)2]-. Attempts to obtain this d 10 species by chemical as well as electrochemical reduction of 1 lead to the hydride HCo(dppf)2, 2, as the only product that can be isolated. Reduction of Ni(dppf)Cl2 with sodium in the presence of dppf and catalytic amounts of naphthalene affords Ni(dppf)2, 3, isolated in 60% yield as a yellow air stable solid. The stoichiometric oxidation of 3 with [FeCp2]PF6 forms the d9 complex [Ni(dppf)2]PF6, 4, which represents the second example of a structurally characterized Ni(I) complex stabilized by phosphines. A single-crystal X-ray analysis shows for the metal a distorted tetrahedral environment with a dihedral angle defined by the planes containing the atoms P(1), Ni, P(2) and P(3), Ni, P(4) of 78.2° and remarkably long Ni-P bond distances (2.342(3)-2.394(3) A). The EPR spectroscopic properties of 1 (at 106 K in THF) and 4 (at 7 K in 2-methyl-THF) have been examined and g tensor values measured (1, gx = 2.008, gy = 2.182, gz = 2.326; 4, gx = 2.098, gy = 2.113, gz = 2.332). A linear dependence between the hyperfine constants and the Ni-P bond distances has been evidenced. Finally, the change with time of the EPR spectrum of 4 indicates that it very slowly releases dppf.