128575-34-8

Usage

Uses

Used in Chemical Synthesis:
(R)-(-)-1,1'-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE) is used as a catalyst for enhancing the stereoselectivity of reactions, such as Michael addition, Aldol reaction, and oxidation, leading to the preparation of enantioenriched compounds with high purity and yield.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-(-)-1,1'-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE) is utilized as a catalyst in the synthesis of chiral drugs, ensuring the production of the desired enantiomer with high selectivity, which is crucial for the biological activity and safety of the final drug product.
Used in Research and Development:
(R)-(-)-1,1'-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE) is employed as a research tool in academic and industrial laboratories for exploring new synthetic routes and developing innovative methodologies in organic chemistry, contributing to the advancement of the field.
Used in Material Science:
In material science, (R)-(-)-1,1'-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE) is used as a catalyst in the synthesis of chiral materials and polymers, enabling the creation of materials with specific properties and functions, such as chiral recognition, self-assembly, and optical activity.
Overall, the unique properties of (R)-(-)-1,1'-BI-2-NAPHTHOL BIS(TRIFLUOROMETHANESULFONATE), including its high stereoselectivity, wide applicability, and relatively low toxicity, make it a valuable asset in various industries, particularly in chemical synthesis, pharmaceuticals, research and development, and material science.

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 335-05-7 Trifluoromethanesulfonyl fluoride 
• 141807-44-5 (+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl 
• 1025373-45-8 trifluoromethanesulfonic acid anhydride 
• 602-09-5 1,1'-bi-2-naphthol 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 108-48-5 2,6-dimethylpyridine 

Downstream Products

• 76144-87-1 (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine) 
• 1523504-20-2 C₃₆H₂₂AuF₆IN₂ 
• 1523504-20-2 C₃₆H₂₂AuF₆IN₂ 
• 1523504-41-7 C₄₂H₂₆AuBrF₆N₂ 
• 1523504-41-7 C₄₂H₂₆AuBrF₆N₂ 
• 76144-87-1 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 
• 19634-89-0 (R)-2,2'-dimethyl-1,1'-binaphthyl 

Relevant academic research and scientific papers

Application of a Ferrocene-Based Palladacycle Precatalyst to Enantioselective Aryl-Aryl Kumada Coupling

The palladium catalysed reaction of 1-iodo-2-methylnaphthalene and 2-methyl-1-naphthylmagnesium bromide gave quantitatively an (Sa)-configured cross-coupled product in 80 % e.e. using (R,Sp)-PPFA as a ligand. N,N-Dimethylaminomethylferrocene was cyclopalladated (Na2PdCl4, (S)?Ac?Phe?OH, 93 % e.e., as determined by 1H NMR as a result of self-induced non-equivalence), and the resulting (Sp)-configured dimeric palladacycle was employed as a precatalyst for this cross-coupling reaction (5 mol%). Addition to the palladacycle of diphenylphosphine and subsequent base-promoted bidentate ligand synthesis and palladium capture gave an in situ generated catalyst resulting in an (Sp)-configured product in up to 71 % e.e.

New bifunctional bis(Azairidacycle) with axial chirality via double cyclometalation of 2,2′-bis(aminomethyl)-1,1’-binaphthyl

As a candidate for bifunctional asymmetric catalysts containing a half-sandwich C-N chelating Ir(III) framework (azairidacycle), a dinuclear Ir complex with an axially chiral linkage is newly designed. An expedient synthesis of chiral 2,2′-bis(aminomethyl)-1,1′-binaphthyl (1) from 1,1-bi-2-naphthol (BINOL) was accomplished by a three-step process involving nickel-catalyzed cyanation and subsequent reduction with Raney-Ni and KBH4. The reaction of (S)-1 with an equimolar amount of [IrCl2Cp*]2 (Cp* = η5-C5(CH3)5) in the presence of sodium acetate in acetonitrile at 80 ?C gave a diastereomeric mixture of new dinuclear dichloridodiiridium complexes (5) through the double C-H bond cleavage, as confirmed by 1H NMR spectroscopy. A loss of the central chirality on the Ir centers of 5 was demonstrated by treatment with KOC(CH3)3 to generate the corresponding 16e amidoiridium complex 6. The following hydrogen transfer from 2-propanol to 6 provided diastereomers of hydrido(amine)iridium retaining the bis(azairidacycle) architecture. The dinuclear chlorido(amine)iridium 5 can serve as a catalyst precursor for the asymmetric transfer hydrogenation of acetophenone with a substrate to a catalyst ratio of 200 in the presence of KOC(CH3)3 in 2-propanol, leading to (S)-1-phenylethanol with up to an enantiomeric excess (ee) of 67%.

The Trityl Cation Embedded into a [7]Helicene-Like Backbone: Preparation and Application as a Lewis Acid Catalyst

The synthesis of a helically chiral carbenium ion is reported. The new motif is essentially a trityl cation embedded into a [7]helicene-like framework. The key step in its preparation establishes the π-extended fluorenone system in one step by an unprecedented palladium-catalyzed carbonylative annulation of a 4,4′-biphenanthryl-3,3′-diyl precursor. The racemic form of the new carbon Lewis acid was found to catalyze a representative set of reactions typically promoted by the trityl cation.

In Situ Generation of Ruthenium Carbonyl Phosphine Complexes as a Versatile Method for the Development of Enantioselective C?O Bond Arylation

We report here a method for in situ generation of various ruthenium carbonyl phosphine catalysts for arylation via cleavage of inert aromatic carbon–oxygen bonds. The use of catalyst systems consisting of [RuCl2(CO)(p-cymene)], CsF, styrene, an

Asymmetric ketone hydroboration catalyzed by alkali metal complexes derived from BINOL ligands

The ability of alkali metal complexes featuring functionalized BINOL-derived ligands to catalyze ketone hydroboration reactions was explored. The reduced products were formed in excellent yields and with variable enantioselectivities dependent upon the nature of the ligand and the alkali metal cation.

Trost ligand with axial chiral binaphthyl skeleton and preparation method thereof

The invention discloses a novel optically pure binaphthyl Trost ligand and a preparation method thereof. (S)-2'-(diarylphosphine)-[1, 1'-binaphthyl]-2-carboxylic acid and chiral diamine are subjectedto condensation reaction to obtain the Trost ligand with

Single-component, low molecular weight organic supergelators based on chiral barbiturate scaffolds

We report here the first chiral barbiturate to act as a single-component LMOG capable of gelating a variety of chlorinated and aromatic solvents. Solution-based DOSY NMR experiments, solid-state VP-SEM, and X-ray crystallography techniques were used to ch

Design of Phosphinic Acid Catalysts with the Closest Stereogenicity at the α-Position: Synthesis and Application of α-Stereogenic Perfluoroalkyl Phosphinic Acid Catalysts

Chiral C2-symmetric phosphinic acids were designed based on sterically demanding and helical chiral perfluoroalkyl groups at the closest α-position advancing asymmetric reaction environment and catalytic activity. The perfluoroalkyl catalysts,

Evaluation of bifunctional chiral phosphine oxide catalysts for the asymmetric hydrosilylation of ketimines

A series of bifunctional phosphine oxides have been prepared and evaluated as catalysts for the trichlorosilane mediated asymmetric hydrosilylation of ketimines. bis-Phosphine oxides, hydroxy-phosphine oxides, and biaryl phosphine oxides all demonstrated good catalytic activity, but poor to moderate enantioselectivity. A bis-P-chiral phosphine oxide displayed the highest enantioselectivity of 60%.

Large Scale Synthesis of Chiral (3 Z,5 Z)-2,7-Dihydro-1H-azepine-Derived Hamari Ligand for General Asymmetric Synthesis of Tailor-Made Amino Acids

An advanced process for large scale (500 g) preparation of a (3Z,5Z)-2,7-dihydro-1H-azepine-derived chiral tridentate ligand (Hamari ligand), widely used for asymmetric synthesis of tailor-made α-amino acids via the corresponding glycine Schiff base Ni(II