84350-73-2

Usage

Uses

Used in Coordination Chemistry:
Tris(2-fluorophenyl)phosphane is used as a ligand for forming complexes with transition metal ions, which enhances the reactivity and selectivity of various chemical reactions. Its unique electronic properties allow for fine-tuning of the metal center's properties, making it a valuable tool in this field.
Used in Organometallic Catalysis:
In organometallic catalysis, tris(2-fluorophenyl)phosphane is employed as a ligand to improve the efficiency and selectivity of catalytic processes. Its steric and electronic characteristics contribute to the stabilization of catalytic intermediates and transition states, facilitating challenging transformations.
Used in Organic Synthesis:
Tris(2-fluorophenyl)phosphane is utilized in organic synthesis for its ability to participate in a variety of reactions, such as cross-coupling and hydrophosphination. Its presence can influence the outcome of reactions, providing access to new synthetic pathways and products.
Used in Materials Science:
In materials science, tris(2-fluorophenyl)phosphane is studied for its potential use in the development of new materials with tailored properties. Its unique structure and properties can be leveraged to create materials with specific electronic, optical, or mechanical characteristics.
Used in Pharmaceutical Development:
Tris(2-fluorophenyl)phosphane is applied in the pharmaceutical industry as a building block or intermediate in the synthesis of new drug candidates. Its unique properties can be harnessed to design molecules with novel biological activities or improved pharmacokinetic profiles.
Used in Agrochemicals:
In the agrochemical sector, tris(2-fluorophenyl)phosphane is used in the development of new pesticides or herbicides. Its chemical versatility allows for the creation of compounds with enhanced efficacy and selectivity against target pests or weeds.
Overall, tris(2-fluorophenyl)phosphane is a multifaceted compound with broad applications across various scientific disciplines, from catalysis to materials science and pharmaceuticals, underscoring its importance in modern chemical research and development.

Upstream product

• 1072-85-1 o-fluorobromobenzene 
• 462-06-6 fluorobenzene 

Downstream Products

• 1337554-65-0 [(η5-C5Me5)Fe(H2PC6H4PH2)(tris(ortho-fluorophenyl)phosphine)]BF4 
• 358725-32-3 [(η5-C5H5)Fe(H2PC6H4PH2)(tris(ortho-fluorophenyl)phosphine)]PF6 

Relevant academic research and scientific papers

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

Electrophilic Phosphonium Cation-Mediated Phosphane Oxide Reduction Using Oxalyl Chloride and Hydrogen

The metal-free reduction of phosphane oxides with molecular hydrogen (H2) using oxalyl chloride as activating agent was achieved. Quantum-mechanical investigations support the heterolytic splitting of H2 by the in situ formed electrophilic phosphonium cation (EPC) and phosphane oxide and subsequent barrierless conversion to the phosphane and HCl. The reaction can also be catalyzed by the frustrated Lewis pair (FLP) consisting of B(2,6-F2C6H3)3 and 2,6-lutidine or phosphane oxide as Lewis base. This novel reduction was demonstrated for triaryl and diaryl phosphane oxides providing access to phosphanes in good to excellent yields (51–93 %).

Effects of phosphorus substituents on reactions of α- alkoxyphosphonium salts with nucleophiles

The effects of phosphorus substituents on the reactivity of α-alkoxyphosphonium salts with nucleophiles has been explored. Reactions of α-alkoxyphosphonium salts, prepared from various acetals and tris(o-tolyl)phosphine, with a variety of nucleophiles proceeded efficiently. These processes represent the first examples of high-yielding nucleophilic substitution reactions of α-alkoxyphosphonium salts. The reactivity of these salts was determined by a balance between steric and electronic factors, respectively, represented by cone angles θ and CO stretching frequencies ν (steric and electronic parameters, respectively). In addition, a novel reaction of α-alkoxyphosphonium salts derived from Ph3P with Grignard reagents was observed to take place in the presence of O2 to afford alcohols in good yields. A radical mechanism is proposed for this process that has gained support from isotope-labeling and radical-inhibition experiments. A dramatic change in the reactivity of an α-alkoxyphosphonium salt toward nucleophiles is observed due to the steric and electronic nature of the phosphine substituents. By changing the type of phosphorus substituents, the reaction pathway can be controlled to proceed selectively by substitution or a new radical reaction (see scheme; OTf=trifluoromethansulfonate, TMS=trimethylsilyl, o-tol=tolyl). Copyright

SYNTHESE UND NMR-UNTERSUCHUNGEN VON 2-FLUOR-TRIPHENYLPHOSPHINEN UND IHREN DERIVATEN

2-Fluorophenyllithium reacts with chloro-phenyl-phosphines PH3-nPCln, n=1,2,3 to give diphenyl-(2-fluorophenyl)phosphine 1, bis-(2-fluorophenyl)phenyl-phosphine 2 and tris-(2-fluorophenyl)phosphine 3.The new compounds and their oxide