67292-34-6

Basic information

• Product Name: [1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II)
• Synonyms: Ni(dppf)Cl2;[1,1'-Bis(diphenylphosphino)ferrocene]nickel(II) chloride, 99%;[1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(Ⅱ);[1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II),98%;Dichloro[1,1'-bis(diphenylphosphino)ferrocene]nickel(II),98% (DPPF)NiCl2;[1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II) Dichloro[1,1'-bis(diphenylphosphino)ferrocene]nickel(II);[1,1'-Bis(diphenylphosphiNA)ferrocene]dichloronickel(II);[1,1'-Bis(diphenylphosphino)fe
• CAS NO: 67292-34-6
• Molecular Formula: C₃₄H₂₈Cl₂FeNiP₂
• Molecular Weight: 683.98
• Product Categories: Ni;Catalysts for Organic Synthesis;Classes of Metal Compounds;Fe (Iron) Compounds;Ferrocenes;Homogeneous Catalysts;Metal Complexes;Metallocenes;Ni (Nickel) Compounds;Synthetic Organic Chemistry;Transition Metal Compounds;Catalysis and Inorganic Chemistry;Chemical Synthesis;Metal Compounds;pharmacetical
• Mol File: 67292-34-6.mol

Chemical Properties

• Melting Point: 285 °C (dec.)(lit.)
• Appearance: green micro/crystal
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: [1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II)(CAS DataBase Reference)
• NIST Chemistry Reference: [1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II)(67292-34-6)
• EPA Substance Registry System: [1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II)(67292-34-6)

Safety Data

• Hazard Codes: T
• Statements: 45-42/43
• Safety Statements: 53-22-36/37/39-45
• RIDADR: 2811
• WGK Germany: 3
• Hazardous Substances Data: 67292-34-6(Hazardous Substances Data)

Usage

Uses

Used in Transition Metal-Catalyzed Reactions:
[1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II) is used as a catalyst in transition metal-catalyzed reactions for the synthesis of pharmaceuticals and agrochemicals. Its ability to facilitate the formation of new chemical bonds and improve reaction efficiency makes it a valuable tool in the development of new drugs and agricultural products.
Used in Gem-Difluoropropargylation of Alkylzinc Reagents:
In the field of organic synthesis, [1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II) is used as a catalyst for the gem-difluoropropargylation of alkylzinc reagents. This reaction allows for the formation of gem-difluorinated propargylic compounds, which are important building blocks in the synthesis of complex organic molecules and have potential applications in various industries.
Used in Cross-Coupling Reactions:
[1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II) is also employed as a catalyst in cross-coupling reactions, enabling the formation of 2,3,5,6-tetrasubstituted dehydropiperidines. These compounds are valuable intermediates in the synthesis of various pharmaceuticals and agrochemicals, showcasing the versatility of this catalyst in organic synthesis.
Used in Suzuki Reaction:
In the realm of palladium-catalyzed cross-coupling reactions, [1,1'-Bis(diphenylphosphino)ferrocene]dichloronickel(II) is used as a catalyst in the Suzuki reaction. This reaction involves the coupling of an organoboron compound with an organohalide, leading to the formation of new carbon-carbon bonds. The Suzuki reaction is widely used in the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.

Upstream product

• 12150-46-8 1,1'-bis-(diphenylphosphino)ferrocene 
• 83864-14-6 nickel dichloride 
• 201230-82-2 carbon monoxide 
• 14264-16-5 bis(triphenylphosphine)nickel(II) chloride 

Downstream Products

• 94202-32-1 (1,1′-bis(diphenylphosphino)ferrocene)₂Ni 
• 1501945-23-8 cis-[1,1'-bis(diphenylphosphino)ferrocene](2-methylphenyl)nickel(II) chloride 
• 162476-91-7 [(1,1′-bis(diphenylphosphino)ferrocene)Ni⁽⁰⁾(1,5-cyclooctadiene)] 
• 160260-01-5 dicarbonyl[bis(diphenylphosphino)ferrocene]nickel⁽⁰⁾ 

Relevant articles and documents

Synthetic, electrochemical, and structural studies on heterobimetallic crown thioether complexes with Group 10 metals: The crystal structures of [Pt(9S3)(dppf)](PF6)2·CH3NO2 and [Pd(9S3)(dppf)](PF6)2·CH3NO2

The syntheses, electrochemistry, and crystal structures for two new Pt(II) and Pd(II) heteroleptic bimetallic complexes with the crown trithioether 1,4,7-trithiacyclononane (9S3) and the diphosphine ligand, 1,1′-bis(diphenylphosphino)ferrocene (dppf) are reported. Both complexes have the general formula [M(9S3)(dppf)](PF6)2 (M=Pt or Pd) and exhibit the anticipated structure forming a distorted cis square planar array of two sulfur atoms from the 9S3 and two phosphorus atoms. These are, to our knowledge, the first reported examples of dppf transition metal complexes involving a thioether as the ancillary ligand. The dppf ligand functions as a bidentate chelator to a single metal center, and the third 9S3 sulfur atom does interact with the metal ion from a greater distance (Pt-S=2.8167(8) ?; Pd-S=2.7916(5) ?) to yield an elongated square pyramidal geometry. The two structures are isomorphous with very similar bond distances and angles. The values for the 31P-NMR chemical shifts (Pt=15.09 ppm, Pd=-0.47 ppm), the 195Pt-NMR chemical shift for the Pt(II) complex (-4353 ppm) and 1J(195Pt-31P) coupling constants (3511 Hz) are all consistent with a cis-MS2P2 square planar coordination sphere. The 9S3 ligand is fluxional in solution for both complexes. The electrochemistry of both complexes is dominated by a reversible Fe(II)/Fe(III) couple from the ferrocene moiety (E1/2=+721 mV for Pt(II), +732 mV for Pd(II), both versus Fc/Fc+).

Selective nickel-catalyzed fluoroalkylations of olefins

Mild and selective nickel-catalyzed trifluoromethylation and perfluoroalkylation reactions of alkenes were developed to provide fluorinated olefins, including natural products, pharmaceuticals, and variety of synthetic building blocks in good to excellent

Efficient catalytic transfer hydrogenation reactions of carbonyl compounds by Ni(II)-diphosphine complexes

The catalytic transfer hydrogenation reactions of a series of aromatic and aliphatic carbonyl compounds were investigated using divalent Ni(II)-diphosphine complexes, [L2NiCl2] (where L2 = 1,1-bis(diphenylphosphino)methane (dppm), 1,2-bis(diphenylphosphino)ethane (dppe), 1,3-bis(diphenylphosphino)propane (dppp), 1,1-bis(diphenylphosphino)ferrocene (dppf), and N-butyl-N-(diphenylphosphino)-1,1-diphenylphosphinamine (dppba)). This is a single-step reaction in the presence of potassium hydroxide and isopropyl alcohol to afford the corresponding alcohols. This protocol tolerates other sensitive functional groups like olefinic double bonds and also achieves high chemoselectivity. All the reactions were monitored by GC and GC–MS. The plausible mechanism is also discussed. The method reported in the present article is simple, cost-effective, and provides excellent conversions. Nickel-diphosphine complexes appear as a potential alternative to expensive transition metal complexes.

METHOD FOR PREPARATION OF FLUORO ALKYLATED COMPOUNDS BY HOMOGENEOUS NI CATALYSIS

The invention discloses a method for the preparation of fluoro alkylated compounds by homogeneous Ni catalyzed fluoro alkylation with fluoro alkyl halides in the presence of a base.

METHOD FOR PREPARATION OF FLUORO ALKYLATED 1,4-DIOXENE BY HOMOGENEOUS NI CATALYSIS

The invention discloses a method for the preparation of fluoro alkylated 1,4-dioxene by homogene- ous Ni catalyzed fluoro alkylation with fluoro alkyl halides of 1,4-dioxane in the presence of a base.

Oxidatively Induced Aryl-CF3 Coupling at Diphosphine Nickel Complexes

This communication describes the synthesis of a series of diphosphine NiII(Ph)(CF3) complexes and studies of their reactivity toward oxidatively induced Ph-CF3 bond-forming reductive elimination. Treatment of these complexes with the one-electron outer-sphere oxidant ferrocenium hexafluorophosphate (FcPF6) affords benzotrifluoride, but the yield varies dramatically as a function of diphosphine ligand. Diphosphines with bite angles of less than 92° afforded 3. In contrast, those with bite angles between 95 and 102° formed PhCF3 in yields ranging from 62 to 77%.

A general and practical Ni-catalyzed C-H perfluoroalkylation of (hetero)arenes

A direct perfluoroalkylation of (hetero)arenes using the air- and moisture-stable complex (dppf)Ni(o-tol)Cl was developed (23 examples). The novel procedure allows for the synthesis of various fluorinated products and tolerates sensitive functional groups including aldehydes, free amino groups and several heterocycles.

General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP

A new and general nickel-catalyzed cyanation of hetero(aryl) chlorides using less toxic Zn(CN)2 as the cyanide source has been developed. The reaction relies on the use of inexpensive NiCl2·6H2O/dppf/Zn as the catalytic system and DMAP as the additive, allowing the cyanation to occur under mild reaction conditions (50-80 °C) with wide functional group tolerance. DMAP was found to be crucial for successful transformation, and the reaction likely proceeds via a Ni(0)/Ni(II) catalysis based on mechanistic studies. The method was also successfully extended to aryl bromides and aryl iodides.

NICKEL PRE-CATALYSTS AND RELATED COMPOSITIONS AND METHODS

Described herein are nickel pre-catalysts and related compositions and methods. The nickel pre-catalysts may be activated to form catalysts which may be utilized in organic reactions.

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.