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Usage

Uses

Used in Pharmaceutical Industry:
S-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol is used as a chiral ligand for controlling the stereochemistry of chemical reactions in the production of pharmaceuticals. Its ability to influence the spatial arrangement of atoms in a molecule is crucial for creating enantiomerically pure compounds, which are essential for the development of effective and safe drugs.
Used in Fine Chemicals Production:
In the fine chemicals industry, S-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol serves as a chiral ligand to ensure the precise control of stereochemistry during the synthesis of high-value specialty chemicals. This is vital for the creation of enantiomerically pure compounds that are used in fragrances, agrochemicals, and other high-demand applications.
Used in Organic Synthesis:
S-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol is utilized as a chiral catalyst or ligand in various organic synthesis processes. Its unique structure and properties make it a versatile component for facilitating asymmetric reactions, leading to the production of enantiomerically enriched products that are important in a wide range of chemical and biological applications.
Used in Catalysis Research:
In the field of catalysis, S-3,3'-diiodo-[1,1'-Binaphthalene]-2,2'-diol is employed as a chiral ligand in the development and study of new catalytic systems. Its role in these systems is to enhance the selectivity and efficiency of catalytic reactions, contributing to the advancement of green chemistry and sustainable processes.

Upstream product

• 394737-28-1 (±)?3,3'?diiodo?2,2'?dimethoxy?1,1'?binaphthalene 
• 103027-41-4 1-(tert-butyldimethylsilyl)-4-(4',4',5',5'-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-5-ol 
• 17295-11-3 methyl 6-hydroxynaphthalene-2-carboxylate 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 
• 142010-88-6 (rac)-3,3’-diiodo-2,2’-di(methoxymethoxy)-1,1’-binaphthyl 
• 602-09-5 1,1'-bi-2-naphthol 
• 75685-01-7 2,2'-dimethoxy-1,1'-binaphthyl 

Downstream Products

• 39215-21-9 [1,1'-binaphthalene]-2,2',3,3'-tetraol 

Relevant academic research and scientific papers

Oxidation of BINOLs by Hypervalent Iodine Reagents: Facile Synthesis of Xanthenes and Lactones

Xanthene derivatives have broad applications in medicines, fluorescent probes, dyes, food additives, etc. Therefore, much attention was focused on developing the synthetic methods to prepare these compounds. Binaphthyl-based xanthene derivatives were prepared through the oxidation of BINOLs promoted by the hypervalent iodine reagent iodosylbenzene (PhIO). Nine-membered lactones were obtained through a similar oxidative reaction when iodoxybenzene (PhIO2) was used. Additionally, one-pot reactions of BINOLs, PhIO and nucleophiles such as alcohols and amines were also investigated to provide alkoxylated products and amides in good to excellent yields.

Aggregation-induced CPL response from chiral binaphthyl-based AIE-active polymers via supramolecular self-assembled helical nanowires

In this paper chiral polymer R-P could be synthesized by click polymerization reaction of (R)-3,3′-diethynyl-2,2′-bis(octyloxy)-1,1′-binaphthalene (R-M-1) and 1,2-bis(4-azidophenyl)-1,2-diphenylethene (M-2), and S-P was obtained by click polymerization re

The amplified circularly polarized luminescence emission response of chiral 1,1′-binaphthol-based polymers via Zn(II)-coordination fluorescence enhancement

Two kinds of chiral 1,1′-binaphthol (BINOL)-based polymer enantiomers were designed and synthesized by the polymerization of 5,5′-((2,2′-bis (octyloxy)-[1,1′-binaphthalene]-3,3′-diyl)bis(ethyne-2,1-diyl))bis(2-hydroxybenzaldehyde) (M1) with alkyl diamine (M2) via nucleophilic addition–elimination reaction. The resulting chiral polymers can exhibit mirror image cotton effects either in the absence or in the presence of Zn2+ ion. Almost no fluorescence or circularly polarized luminescence (CPL) emission could be observed for two chiral BINOL-based polymer enantiomers in the absence of Zn2+. Interestingly, the chiral polymers can show strong fluorescence and CPL response signals upon the addition of Zn2+, which can be attributed to Zn2+-coordination fluorescence enhancement effect. This work can develop a new strategy on the design of the novel CPL materials via metal-coordination reaction.

Doping-free circularly polarized electroluminescence of AIE-active chiral binaphthyl-based polymers

AIE-active chiral polymer enantiomers (S-/R-P) can emit green circularly polarized electroluminescence (CP-EL) with gEL up to 0.024 without alignment layers and chiral dopants, which represents the first example of CP-OLEDs based on AIE-active

Aerobic oxidative coupling of 2-naphthol derivatives catalyzed by a hexanuclear bis(μ-hydroxo)copper(II) catalyst

A novel hexanuclear bis(μ-hydroxo)copper(II) complex, [L3(Cu2(μ-OH)2)3](ClO4)6 (1), was synthesized with dinucleating ligand N,N,N,N-tetra(pyridin-2-ylmethyl)-m-xylene diamine (L). Complex 1 is fully characterized by X-ray crystallography and magnetic susceptibility in the solid state and UV-vis and electron paramagnetic resonance spectroscopy in solution. The molecular structure of 1 possesses three dicopper cores, in which two copper centers are bridged by two hydroxide groups and separated by a distance ranging from 2.8852(15) to 2.8937(10) ?. In addition, the three dicopper cores are linked by the dinucleating ligand between each pair of adjacent dicopper cores. Importantly, aerobic oxidative coupling of 2,4-di-tert-butylphenol, 2-naphthol, and six 2-naphthol derivatives was achieved in 33-96% yield using complex 1 as a catalyst.

Enantioenriched synthesis of C 1-symmetric BINOLs: Iron-catalyzed cross-coupling of 2-naphthols and some mechanistic insight

Highly enantioselective aerobic oxidative cross-coupling of 2-naphthols with broad substrate scope was achieved using an iron(salan) complex as the catalyst. Enantiomeric excesses of the products ranged from 87 to 95%. The scope of the cross-coupling reac

Chiral metallacyclophanes: Self-assembly, characterization, and application in asymmetric catalysis

(Equation presented) A family of chiral metallacyclophanes has been readily assembled based on robust Pt-acetylide linkage and characterized by a variety of spectroscopic techniques and X-ray crystallography. The steric congestion around the chiral dihydr