348617-10-7

Basic information

• Product Name: (R)-2-Diphenyphosphino-2'-phenyl-1,1'-binaphthyl
• Synonyms: (r)-2-diphenyphosphino-2'-phenyl-1,1'-binaphthyl;(R)-(+)-2-DIPHENYLPHOSPHINO-2'-PHENYL-1,1'-BINAPHTHYL
• CAS NO: 348617-10-7
• Molecular Formula: C38H27P
• Molecular Weight: 514.59
• Product Categories: API intermediates
• Mol File: 348617-10-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-2-Diphenyphosphino-2'-phenyl-1,1'-binaphthyl(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Diphenyphosphino-2'-phenyl-1,1'-binaphthyl(348617-10-7)
• EPA Substance Registry System: (R)-2-Diphenyphosphino-2'-phenyl-1,1'-binaphthyl(348617-10-7)

Safety Data

• Hazardous Substances Data: 348617-10-7(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Catalysis:
(R)-2-Diphenyphosphino-2'-phenyl-1,1'-binaphthyl is used as a chiral ligand for asymmetric catalysis to facilitate enantioselective reactions. Its application is essential for the production of chiral molecules with high enantiomeric purity, which are vital in various pharmaceutical and chemical industries.
Used in Organic Synthesis:
In the field of organic synthesis, (R)-2-Diphenyphosphino-2'-phenyl-1,1'-binaphthyl is used as a catalyst in various catalytic processes, such as cross-coupling reactions, hydrogenation, and cycloadditions. Its unique structure allows it to interact efficiently with metal catalysts and substrates, enabling the selective formation of chiral products.
Used in Pharmaceutical Industry:
(R)-2-Diphenyphosphino-2'-phenyl-1,1'-binaphthyl is used as a key component in the development of enantioselective synthetic methods for the production of chiral pharmaceuticals. The ability to produce chiral compounds with high enantiomeric purity is crucial for the synthesis of effective and safe drugs.
Used in Chemical Industry:
In the chemical industry, (R)-2-Diphenyphosphino-2'-phenyl-1,1'-binaphthyl is utilized as a catalyst in the synthesis of chiral compounds for various applications, including agrochemicals, fragrances, and specialty chemicals. Its ability to promote enantioselective reactions contributes to the efficient and selective production of these compounds.
Overall, (R)-2-Diphenyphosphino-2'-phenyl-1,1'-binaphthyl is a valuable tool in the fields of asymmetric catalysis, organic synthesis, and the production of chiral compounds, making it indispensable for the development of innovative synthetic methods and the creation of important chiral products across various industries.

Upstream product

• 1079-66-9 chloro-diphenylphosphine 
• 108-86-1 bromobenzene 
• 264188-44-5 (S)-2-diphenylphosphino-1,1'-binaphthyl 
• 55441-97-9 <1,1'-Binaphthalene>-2,2'-diyl O,O-bis(N,N-dimethylthiocarbamate) 
• 100-58-3 phenylmagnesium bromide 
• 194-65-0 1,1'-binaphthothiophene 

Relevant articles and documents

Preparation method for aryl-substituted biphenyl, pyrrole, indol or binaphthyl monophosphine ligand

The invention discloses a preparation method for a new-style monophosphine ligand. The method comprises the following process: (a) by taking a commercialized biphenyl, pyrrole, indol or binaphthyl monophosphine ligand as a raw material, under the protection of inert gas, controlling the reaction temperature to be 70-150 DEG C in an organic solution under the participation of an inorganic base, and carrying out monovalent rhodium catalysis on the raw material and an aromatic halogenated compound to prepare the new-style aryl-substituted biphenyl, pyrrole, indol or binaphthyl monophosphine ligand. The synthetic route is not reported in literature, and the raw material is cheap and easily available; and the unit operation is simple, and the requirement on equipment is low, so that the preparation method is suitable for quickly constructing a new-style monophosphine ligand library.

Rhodium(I)-Catalyzed Tertiary Phosphine Directed C?H Arylation: Rapid Construction of Ligand Libraries

Modification of commercially available monophosphine ligands with either aryl bromides or chlorides by rhodium(I)-catalyzed, tertiary phosphine directed C?H activation is described. A series of ligand libraries containing mono- and diaryl-substituted groups, having different steric and electronic properties, were obtained in high yields. Based on the outstanding properties of their parent scaffolds, the modified ligands have been found to be powerful in organic reactions.

Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses

Several novel chiral N-heterocyclic carbene and phosphine ligands were prepared from (S)-BINOL. Moreover, their ligated Au complexes were also successfully synthesized and characterized by X-ray crystal diffraction. A weak gold-π interaction between the Au atom and the aromatic ring in these gold complexes was identified. Furthermore, we confirmed the formation of a pair of diastereomeric isomers in NHC gold complexes bearing an axially chiral binaphthyl moiety derived from the hindered rotation around C-C and C-N bonds. In the asymmetric intramolecular hydroamination reaction most of these chiral Au(I) complexes showed good catalytic activities towards olefins tethered with a NHTs functional group to give the corresponding product in moderate yields and up to 29% ee.

Asymmetric synthesis of axially chiral biaryls by nickel-catalyzed Grignard cross-coupling of dibenzothiophenes

Catalytic asymmetric Grignard cross-coupling of 1,9-disubstituted dibenzothiophenes (6a-c) and dinaphthothiophene (6d) with aryl- and alkyl-Grignard reagents (7) proceeded with high enantioselectivity (up to 95% ee) in the presence of a nickel catalyst (3-6 mol %) coordinated with 2-diphenylphosphino-1,1′-binaphthyl (H-MOP) or oxazoline-phosphine ligand (i-Pr-phox) in THF to give 2-mercapto-2′-substituted-1,1′-biphenyls (8a-c) and 2-mercapto-2′-substituted-1,1′-binaphthyls (8d) in high yields. The mercapto group in the axially chiral cross-coupling products was converted into several functional groups by way of the methylsulfinyl group. The rate of flipping in dinaphthothiophene was measured by variable-temperature 31P NMR analysis of methyl-phenylphosphinyldinaphthothiophene derivative (21).

Nickel-catalyzed asymmetric Grignard cross-coupling of dinaphthothiophene giving axially chiral 1,1′-binaphthyls

Asymmetric cross-coupling of dinaphtho[2,1-b:1′,2′-d]thiophene with ArMgBr (Ar = Ph, 4-MeC6H4, 4-MeOC6H4) proceeded withhigh enantioselectivity in THF at 20 °C in the presence of 3 mol % of a nickel catalyst gen

Modification of Chiral Monodentate Phosphine Ligands (MOP) for Palladium-Catalyzed Asymmetric Hydrosilylation of Cyclic 1,3-Dienes

Several MOP ligands 5 containing aryl groups at 2′ position of (R)-2-(diphenylphosphino)-1,1′-binaphthyl skeleton were prepared and used for palladium-catalyzed asymmetric hydrosilylation of cyclic 1,3-dienes 6 with trichlorosilane. Highest enantioselectivity was observed in the reaction of 1,3-cyclopentadiene (6a) catalyzed by a palladium complex (0.25 mol %) coordinated with (R)-2-(diphenylphosphino)-2′-(3,5-dimethyl-4-methoxyphenyl)-1,1′- binaphthyl (5f), which gave (S)-3-(trichlorosilyl)cyclopentene of 90% ee.