13685-91-1

Usage

Uses

Used in Pharmaceutical Industry:
(Diethylamino)bis(4-trifluoromethylphenyl)phosphane is used as a ligand for the development of novel pharmaceutical compounds. Its strong electron-donor characteristics and ability to form stable complexes with transition metals contribute to the enhancement of drug efficacy and selectivity.
Used in Materials Science:
In the field of materials science, (Diethylamino)bis(4-trifluoromethylphenyl)phosphane is used as a stabilizing agent for the synthesis of advanced materials. Its coordination chemistry properties allow for the creation of materials with tailored properties, such as improved stability and reactivity.
Used in Catalysis:
(Diethylamino)bis(4-trifluoromethylphenyl)phosphane is employed as a catalyst or a component in catalytic systems for various chemical reactions. Its electron-donor nature and coordination capabilities enable it to facilitate complex reactions, leading to improved reaction rates and selectivity.
Overall, (Diethylamino)bis(4-trifluoromethylphenyl)phosphane, with its unique properties and applications, plays a significant role in the advancement of pharmaceuticals, materials science, and catalysis, showcasing its potential for further research and development in these industries.

Upstream product

• 1069-08-5 diethylphosphoramidous dichloride 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 

Downstream Products

• 13685-24-0 bis(4-trifluoromethylphenyl)phosphine chloride 
• 15929-43-8 bis(4-(trifluoromethyl)phenyl)phosphine oxide 
• 820253-15-4 2,2'-bis-[bis-(4-trifluoromethyl-phenyl)-phosphinoyl]-[1,1']binaphthalenyl 
• 820253-13-2 bis[4-(trifluoromethyl)phenyl]phosphinyl chloride 

Relevant academic research and scientific papers

Catalytic asymmetric intramolecular hydroamination of alkynes in the presence of a catalyst system consisting of Pd(0)-methyl Norphos (or tolyl Renorphos)-benzoic acid

(Chemical Equation Presented) Enantiomerically pure methyl Norphos (A), tolyl Norphos (B), CF3 Norphos (C), methyl Renorphos (D), and tolyl Renorphos (E) were synthesized and used as chiral bisphosphine ligands for the catalyst system, Pd2(dba)3·CHCl3/PhCOOH, in an intramolecular hydroamination of aminoalkynes 15. Among the Norphos series, methyl Norphos (A) was the best ligand for the hydroamination, and the corresponding five- and six-membered nitrogen heterocycles 16 were obtained in high yields with high enantioselectivities. Among the Renorphos series, tolyl Renorphos (E) gave the best result; both methyl Norphos (A) and tolyl Renorphos (E) afforded high yields and high enantioselectivities. NMR investigation using Me-Norphos revealed that this ligand was oxidized gradually in the presence of Pd2(dba)3·CHCl3 in C6D 6 even under the conditions using Ar atmosphere to give Me-Norphos oxide, which prevented the intramolecular hydroamination. On the other hand, Me-Norphos was rather stable in C6D6 in the absence of the palladium catalyst under Ar atmosphere and was not converted to its oxide even after 3 days. The gradual oxidation of ligands (A and E) in the presence of the Pd catalyst is perhaps a reason why 20 mol % of A or E was needed to obtain high yields and high ee's of 16.

Chiral diphosphorus compounds and their transition metal complexes

The present invention relates to chiral diphosphorus compounds and their transition metal complexes, to a process for preparing chiral diphosphorus compounds and their transition metal complexes and also to their use in asymmetric syntheses.

Rhodium-catalyzed dehydrocoupling of fluorinated phosphine-borane adducts: Synthesis, characterization, and properties of cyclic and polymeric phosphinoboranes with electron-withdrawing substituents at phosphorus

The dehydrocoupling of the fluorinated secondary phosphine-borane adduct R2PH·BH3 (R = p-CF3C6H 4) at 60°C is catalyzed by the rhodium complex [{Rh(μ-Cl)(1,5-cod)}2] to give the four-membered chain R

Stereospecific deoxygenation of phosphine oxides with retention of configuration using triphenylphosphine or triethyl phosphite as an oxygen acceptor

(Chemical Equation Presented) A new protocol for deoxygenation of various phosphine oxides with retention of configuration is described. The advantage of the new method includes milder conditions and considerably shortened reaction times. Mechanistic studies about the oxygen transfer between the starting phosphine oxide and the sacrificial triphenylphosphine are also presented.

Chiral diphosphorus compounds and transition metal complexes thereof

Tetrahydrofuran bisphosphines of formula (I), are new. Tetrahydrofuran bisphosphines of formula (I): X1, X2 = bonds or O; R1, R2 = H, 1-20C alkyl, 1-20C fluoroalkyl, 2-20C alkenyl, 4-24C aryl, 5-25C aralkyl, 6-26C aralkenyl, NR7R8, OR8, AOR8, ANR7R8 or OC

Carbohydrate Phosphinites as Practical Ligands in Asymmetric Catalysis: Electronic Effects and Dependence of Backbone Chirality in Rh-Catalyzed Asymmetric Hydrogenations. Synthesis of R- or S-Amino Acids Using Natural Sugars as Ligand Precursors

Vicinal diarylphosphinites derived from carbohydrates are excellent ligands for the Rh(I)-catalyzed enantioselective asymmetric hydrogenation of dehydroamino acid derivatives, producing the highest enantioselectivity of any ligands directly prepared from natural products. The enantioselectivity can be enhanced by the appropriate choice of substituents on the aromatic rings of the phosphinites. For example, the use of phosphinites with electron-donating bis(3,5-dimethylphenyl) groups on phosphorus provides ee's up to 99% for a wide range of amino acids including some with easily removable N-protecting groups. Electron-withdrawing aryl substituents, on the other hand, decrease the enantioselectivity. Sense of chiral induction in the amino acid product depends on the relative juxtaposition of the vicinal diphosphinites on a given sugar backbone. When readily available D-glucopyranosides are used as the starting sugars, 2,3-phosphinites give the S-amino acids and 3,4-phosphinites give the R-amino acids. In the case of aromatic and heteroaromatic amino acids, enantioselectivities > 95% are consistently obtained. Practical considerations such as the ease of ligand synthesis, rates of reactions, catalyst turnover, and scope and limitations in terms of substrates are discussed. A possible explanation for the enhancement of enantioselectivity by electron-rich phosphinites is offered.

Ligand Electronic Effects in Asymmetric Catalysis: Enhanced Enantioselectivity in the Asymmetric Hydrocyanation of Vinylarenes

The enantioselectivity of the nickel-catalyzed, asymmetric hydrocyanation of vinylarenes using glucosederived, chiral phosphinite ligands, L, increases dramatically when the ligands contain electron-withdrawing P-aryl substituents.The substrate and solvent also strongly influence the enantioselectivity, with the highest ee's (85-91percent for 6-methoxy-2-vinylnaphthalene (MVN)) obtained for the hydrocyanation of electron-rich vinylarenes in a nonpolar solvent such as hexane.Mechanistic studies suggest the catalytic cycle consists of an initial HCN oxidative addition or vinylarene coordination to "NiL", followed by insertion to form an (η3-benzyl)nickel cyanide complex, and irreversible reductive elimination of the nitrile.A kinetic analysis of the NiLa(COD) (La, P-aryl=3,5-(CF3)2C6H3) catalyzed hydrocyanation of MVN indicates that as the HCN concentration is increased the catalyst resting state shifts from NiLa(COD) to a complex containing both MVN and HCN, presumably the (η3-benzyl)nickel cyanide intermediate NiLa(η3-CH3CHC10H6OCH3)CN.A 31P NMR analysis of the intermediate NiLa(MVN) shows little ground state differentiation of the MVN enantiofaces and suggests that the enantioselectivity is determined later in the mechanism.Deuterium labeling studies suggest that electron-withdrawing P-aryl substituents increase the rate of reductive elimination of the product nitrile from the (η3-benzyl)nickel cyanide intermediate and, on this basis, a rationale for the ligand electronic effect is proposed.