75640-87-8

Usage

Chemical Properties

white to off-white crystalline powder

Upstream product

• 93-04-9 2-Methoxynaphthalene 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 74-88-4 methyl iodide 
• 75685-01-7 2,2'-dimethoxy-1,1'-binaphthyl 
• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 77-78-1 dimethyl sulfate 
• 104116-17-8 2-methoxynaphthalene-1-boronic acid 
• 90-13-1 1-Chloronaphthalene 
• 13101-92-3 1-chloro-2-methoxynaphthalene 
• 13922-41-3 1-Naphthylboronic acid 
• 90-14-2 1-Iodonaphthalene 

Downstream Products

• 75714-60-2 (S)-3-bromo-1-(3-bromo-2-methoxynaphthalen-1-yl)-2-methoxynaphthalene 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 
• 874948-59-1 (S)-(-)-3,3’-bisphenyl-1,1’-bi-2-naphthyl phosphoric acid 
• 1170736-59-0 C₃₆H₂₉O₄P 
• 215433-51-5 (S)-3,3’-bis(3,5-dimethylphenyl)-[1,1‘-binaphthalene]-2,2’-diol 

Relevant academic research and scientific papers

Enhancing the enantioselective recognition and sensing of chiral anions by halogen bonding

Chiral halogen bonding (S)-BINOL-based receptors are demonstrated to enhance the enantioselective recognition and sensing of chiral anions compared to their hydrogen bonding analogues. Computational studies attribute this behaviour to the strict linearity of halogen bonding (XB) and steric environment conferred by the XB donor groups bridged by the (S)-BINOL motif.

Unexpected self-assembly of chiral triangles from 90 chiral Di-Pt(II) acceptors

Two unexpected chiral organometallic triangles rather than squares from newly designed 90 chiral di-Pt(II) acceptors were obtained through coordination-driven self-assembly. Their structures were well characterized by multinuclear NMR (1H and 31P) and variable-temperature NMR experiments, ESI-TOF-MS, and elemental analysis. The PM6 semiempirical molecular simulation was employed for the interpretation of the formation and stability of such chiral triangles.

A Chiral, Dendralenic C-H Acid

We report the synthesis of a chiral dendralenic C H acid, which contains three unsubstituted binaphthyl moieties. This motif and an achiral variant can be made from their corresponding bis(sulfone) precursors in one step. Despite the presence of the enantiopure binaphthyl backbone, the newly designed chiral C H acid showed only poor enantioselectivity in a Mukaiyama aldol reaction. First attempts toward the synthesis of 3,3'-hexasubstituted binaphthyl-based dendralenic acids are also reported.

Palladium compound, preparation method thereof and preparation method of axially chiral biaromatic compound

The invention provides a palladium compound, a preparation method thereof and a preparation method of an axially chiral biaromatic compound. The invention discloses a compound shown as a formula IV ora formula IV', the palladium compound is novel in structure and suitable for coupling reaction, and the synthesized axially chiral biaryl compound is diversified in structure, high in yield and goodin stereoselectivity. The invention also discloses a preparation method of the axially chiral biaromatic compound, the axially chiral biaromatic compound prepared by the preparation method has the advantages of high yield, strong reaction stereoselectivity, wide substrate applicability and good applicability to heterocyclic substrates, the ee value can reach 85% or above, most of the ee value is 90% or above, and the substrate is wide in applicability and has very good applicability to heterocyclic substrates; the synthesized axially chiral biaromatic compound has various structures.

Synthesis of Chiral 3,3?-Disubstituted (S)-BINOL Derivatives via the Kumada and Suzuki Coupling and Their Antibacterial Activity

Abstract: A new series of 3,3?-disubstituted chiral (S)-BINOL derivatives 6a–6k has been synthesized viathe Kumada and Suzuki–Miyaura coupling reactions using (S)-BINOL as the initial compound. The Kumada coupling has beenfound to be superior in terms of

Enantioselective cross-coupling for axially chiral tetra-ortho-substituted biaryls and asymmetric synthesis of gossypol

The axially chiral tetra-ortho-substituted biaryl skeleton exists in numerous biologically important natural products, pharmaceutical molecules, chiral catalysts, and ligands. The efficient synthesis of chiral tetra-ortho-substituted biaryl structures rem

Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers

A scalable enantioselective nickel-catalyzed electrochemical reductive homocoupling of aryl bromides has been developed, affording enantioenriched axially chiral biaryls in good yield under mild conditions using electricity as a reductant in an undivided cell. Common metal reductants such as Mn or Zn powder resulted in significantly lower yields in the absence of electric current under otherwise identical conditions, underscoring the enhanced reactivity provided by the combination of transition metal catalysis and electrochemistry.

Enantioselective aryl-aryl coupling facilitated by chiral binuclear gold complexes

Herein, we report stoichiometric investigations embodying the first highly enantioselective aryl-aryl coupling facilitated by a gold complex. With up to 91% ee, this is the first demonstration of a transmetalation and C(sp2)-C(sp2) r

A Bulky Chiral N-Heterocyclic Carbene Palladium Catalyst Enables Highly Enantioselective Suzuki-Miyaura Cross-Coupling Reactions for the Synthesis of Biaryl Atropisomers

Axially chiral biaryl scaffolds are essential structural units in chemistry. The asymmetric Pd-catalyzed Suzuki-Miyaura cross-coupling reaction has been widely recognized as one of the most practical methods for constructing atropisomers of biaryls. However, longstanding challenges remain in this field. For example, substrate scope is often narrow and specialized, functional groups and heterocycles can lead to reduced reactivity and selectivity, bulky ortho-substituents are usually needed, and reported methods are generally inapplicable to tetra-ortho-substituted biaryls. We have developed an unprecedented highly enantioselective N-heterocyclic carbene (NHC)-Pd catalyzed Suzuki-Miyaura cross-coupling reaction for the synthesis of atropisomeric biaryls. These reactions enable efficient coupling of aryl halides (Br, Cl) or aryl triflates with various types of aryl boron compounds (B(OH)2, Bpin, Bneo, BF3K), tolerate a remarkably broad scope of functional groups and heterocycles (>41 examples), employ low loading of catalyst (0.2-2 mol %), and proceed under mild conditions. The protocol provided general and efficient access to various atropisomeric biaryls and heterobiaryls in excellent enantioselectivities (up to 99% ee) with no need of using bulky ortho-substituted substrates and was effective for the synthesis of tetra-ortho-substituent biaryls. Moreover, the method was successfully applied to the diastereo- and enantioselective synthesis of atropisomeric ternaphthalenes. Critical to the success of the reaction is the development and application of an extremely bulky C2-symmetric chiral NHC, (R,R,R,R)-DTB-SIPE, as the ligand for palladium. To the best of our knowledge, this is the first highly enantioselective (>90% ee) example of a chiral NHC-metal-catalyzed C(sp2)-C(sp2) cross-coupling reaction.

Synthesis and catalytic activity of chiral dicarbene dipalladium complexes incorporating the S-binaphthol unit

A series of chiral di-N-heterocyclic carbene (NHC) dipalladium complexes, [{PdPyCl2}2(di-NHC)], in which di-NHC represents a diimidazolylidene, featuring an (S)-3,3'-dimethyl-2,2'-dimethoxy-1,1'-binaphthalene spacer between the carbene units, have been prepared. The influence of ligand size on the catalytic activity of these complexes in the Suzuki reaction of phenylboronic acid with p-bromotoluene has been investigated. The most sterically hindered complex, bearing the di-isopropylphenyl group, showed the greatest catalytic activity, and it is active for various aryl halides with different electronic and steric properties.