132548-91-5

Usage

Uses

Used in Asymmetric Catalytic Reactions:
[1,1'-Binaphthalen]-2-ol, 2'-(diphenylphosphinyl)-, (1R)is used as a chiral ligand for enhancing the selectivity and efficiency of various asymmetric catalytic reactions. Its application is crucial in achieving the desired enantiomeric excess, which is essential for the synthesis of biologically active compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, [1,1'-Binaphthalen]-2-ol, 2'-(diphenylphosphinyl)-, (1R)is used as a catalyst for the enantioselective synthesis of a variety of compounds. This ability is vital for producing single-enantiomer drugs, which can have significant implications on the drug's efficacy and safety.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, [1,1'-Binaphthalen]-2-ol, 2'-(diphenylphosphinyl)-, (1R)is employed as a catalyst for the enantioselective synthesis of active ingredients in pesticides and other agrochemical products. This ensures the production of enantiomerically pure compounds, which can help reduce environmental impact and improve the effectiveness of these products.

Upstream product

• 194-63-8 dinaphtho[2,1-b;1',2'-d]furan 
• 1499-21-4 Diphenylphosphinic chloride 
• 132532-07-1 [1,1'-binaphthalen]-2-yldiphenylphosphine oxide 
• 90948-03-1 1-bromo-2-iodonaphthalene 
• 1589518-11-5 (1-bromonaphthalen-2-yl)diphenylphosphine oxide 
• 4559-70-0 Diphenylphosphine oxide 
• 141807-44-5 (+/-)-2,2'-bis(trifluoromethanesulfonyloxy)-1,1-binaphthyl 
• 602-09-5 1,1'-bi-2-naphthol 
• 199681-29-3 Diphenyl-(2'-trimethylsilanyloxy-[1,1']binaphthalenyl-2-yl)-phosphane 
• 149917-88-4 (S)-(-)-2-hydroxy-2'-diphenylphosphino-1,1'-binaphthyl 
• 132532-04-8 (R)-2-diphenylphosphinyl-2'-trifluoromethanesulfonyloxy-1,1'-binaphthalene 
• 100-58-3 phenylmagnesium bromide 
• 24630-80-6 diphenylphosphine oxide 
• 128544-05-8 (R)-(-)-1,1'-bi-2-naphthol triflate 

Downstream Products

• 194-65-0 1,1'-binaphthothiophene 
• 137769-27-8 (S)-(-)-2-(diphenylphosphinyl)-2'-isopropoxy-1,1'-binaphthyl 
• 137769-29-0 (S)-2-(diphenylphosphinyl)-2'-ethyl-1,1'-binaphthyl 
• 137769-28-9 (S)-(-)-2-(diphenylphosphinyl)-2'-benzyloxy-1,1'-binaphthyl 
• 149917-88-4 (S)-(-)-2-hydroxy-2'-diphenylphosphino-1,1'-binaphthyl 
• 162426-76-8 2-(diphenylphosphinyl)-1,1'-binaphth-2'-ol-N,N-dimethylthiocarbamate 
• 213314-16-0 2'-diphenylphosphinyl-2-hydroxy-6-bromo-1,1'-binaphthalene 
• 162305-89-7 (R,S)-2-(diphenylphosphanyl)-1,1'-binaphthyl-2'-thiol 

Relevant academic research and scientific papers

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.

Axially Chiral Biaryl Monophosphine Oxides Enabled by Palladium/WJ-Phos-Catalyzed Asymmetric Suzuki-Miyaura Cross-coupling

A highly enantioselective palladium/WJ-Phos-catalyzed Suzuki-Miyaura coupling reaction for efficient construction of axially chiral biaryl monophosphine oxides was developed. A series of axially chiral biaryl monophosphine oxides were obtained in good yields and with high enantioselectivities. The practicability of this reaction was validated in the straightforward synthesis of axially chiral biaryl monophosphine ligand and demonstrated by a 100-g-scale synthesis. Moreover, various functionalizations of the product make it as a platform molecule for synthesis of other chiral biaryl phosphines.

Chiral Bifunctional Phosphine-Carboxylate Ligands for Palladium(0)-Catalyzed Enantioselective C?H Arylation

Previous enantioselective Pd0-catalyzed C?H activation reactions proceeding via the concerted metalation-deprotonation mechanism employed either a chiral ancillary ligand, a chiral base, or a bimolecular mixture thereof. This study describes th

Palladium-catalyzed R2(O)P-directed C(sp2)-H activation

In recent years, transition-metal-catalyzed inert C-H bond activation has developed rapidly and is a powerful protocol for the construction of new C-C or C-X bonds and the introduction of new functional groups. Our group has also developed a series of R2(O)P-directed Pd-catalyzed C-H functionalizations involving olefination, hydroxylation, acetoxylation, arylation, and acylation through an uncommon seven-membered cyclo-palladium pretransition state. Unlike previously used directing groups, the R2(O)P group acts as a directing group and is also involved in the construction of P,-hetero-ligands.

Palladium-catalyzed R2(O)P directed C(sp2)-H acetoxylation

A novel and efficient Pd-catalyzed C-H acetoxylation is described. The approach uses R2(O)P as a directing group to synthesize various substituted 2′-phosphorylbiphenyl-2-OAc compounds. Notably, the reaction exhibits smooth operation under mild conditions and shows good functional group tolerance. Products are obtained with high selectivity and yields. This journal is the Partner Organisations 2014.

Pd(II)-catalyzed C(sp2)-H hydroxylation with R 2(O)P-coordinating group

A novel R2(O)P-directed Pd(II)-catalyzed C-H hydroxylation to synthesize various substituted 2′-phosphorylbiphenyl-2-ol compounds is described. Notably, the reaction operates under mild conditions and shows good functional group tolerance, high selectivity, and yield.

Chiral phosphine-catalyzed enantioselective construction of γ-butenolides through substitution of morita-baylis-hillman acetates with 2-trimethylsilyloxy furan

Chiral multifunctional phosphine (R)-N-(2′-diphenylphosphanyl-[1,1-]binaphthalenyl-2-yl)methanesulfonamide L2 or (R)-N-(2′-diphenylphosphanyl-[1,1-]binaphthalenyl-2-yl)acetamide L3 is an efficient catalyst in the allylic substitutions of MBH acetates 1 with 2-trimethylsilyloxy furan 2 to provide γ-butenolides 3 in good to excellent yields and enantiomeric excesses in the presence of water. Copyright

Dendritic chiral phosphine lewis bases-catalyzed asymmetric aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with activated olefins

A series of polyether dendritic chiral phosphine Lewis bases was synthesized, and successfully applied to the asymmetric aza-Morita - Baylis - Hill -man reaction of N - sulfonated imines (N - arylmethyl -idene-4- methylbenzenesulfonamides) with methyl vin

Enantioselective conjugate addition of diethylzinc to acyclic enones using a copper phosphino-phenol complex as catalyst

Newly designed phosphino-phenol 1c was found to be an efficient chiral auxiliary for copper-mediated asymmetric conjugate addition of diethylzinc to acyclic enones. High enantioselectivity up to >99% ee was achieved in the reaction of acyclic α,β-enones.

Palladium-catalyzed asymmetric allylic substitutions by axially chiral P,S-, S,S-, and S,O-heterodonor ligands with a binaphthalene framework

Axially chiral P,S-heterodonor ligand L1 is quite effective in the asymmetric allylic substitution of 1,3-diphenylpropenyl acetate with dimethyl malonate. Its bidentate coordination pattern to Pd metal center with both P and S atoms has been unambiguously established by X-ray diffraction and NMR spectroscopic analyses. Axially chiral P,S-heterodonor ligand L1 is effective in the asymmetric allylic substitution of 1,3-diphenylpropenyl acetate with dimethyl malonate. Its bidentate coordination pattern to a Pd metal center with both P and S atoms has been unambiguously established by X-ray diffraction and NMR spectroscopic analyses. Herein, we further disclose that axially chiral S,S-heterodonor ligands L2-L4 are also effective in the same reaction to give the allylic alkylation product in moderate to good ee. However, the corresponding S,O-heterodonor ligands are not as effective as the corresponding P,S- or S,S-heterodonor ligands in the same asymmetric reaction.