75685-01-7

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
(R)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL is used as a chiral ligand for asymmetric synthesis and catalysis reactions in the pharmaceutical and agrochemical industries. Its unique structure and chirality enable the production of enantiomerically pure compounds, which are essential for the development of effective and safe drugs and agrochemicals.
Used in Chemical Catalysis:
In the field of chemical catalysis, (R)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL is employed as a ligand to form metal complexes that act as catalysts in various chemical transformations. Its ability to selectively bind with metal ions enhances the efficiency and selectivity of catalytic processes, leading to improved yields and reduced environmental impact.
Used in Optical and Electronic Applications:
(R)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL is utilized in the development of optical and electronic materials due to its unique optical properties. Its potential applications in this industry include the creation of advanced optical devices, sensors, and electronic components that leverage its chiral and optical characteristics for enhanced performance and functionality.
Overall, (R)-(+)-2,2'-DIMETHOXY-1,1'-BINAPHTHYL is a multifaceted compound with a wide range of applications across various industries, making it a valuable asset in the fields of chemistry and materials science.

Upstream product

• 32721-21-4 1-iodo-2-methoxynapthalene 
• 93-04-9 2-Methoxynaphthalene 
• 3401-47-6 1-bromo-2-methoxynaphthalene 
• 104116-17-8 2-methoxynaphthalene-1-boronic acid 
• 73183-34-3 bis(pinacol)diborane 
• 591-50-4 iodobenzene 
• 18531-94-7 (+)-2,2'-dihydroxy-1,1'-binaphthyl 
• 77-78-1 dimethyl sulfate 
• 602-09-5 (-)-2,2'-dihydroxy-1,1'-binaphthyl 

Downstream Products

• 75640-69-6 (S)-3,3'-dibromo-2,2'-dimethoxy-1,1'-binaphthalene 
• 144970-05-8 (+/-)-2-hydroxy-2'-methoxy-<1,1'-binaphthalene>-3-carboxaldehyde 
• 141779-46-6 2,2’-dihydroxy-[1,1’-binaphthalene]-3,3’-dicarbaldehyde 
• 121999-12-0 (R)-2,2'-bis(methoxy)-1,1'-binaphthyl-3,3'-dicarbaldehyde 
• 159828-78-1 (R,S)-2,2'-dimethoxy-3-formyl-1,1'-binaphthol 
• 602-09-5 1,1'-bi-2-naphthol 
• 35294-28-1 (R)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 75640-87-8 (S)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 630126-21-5 rac-3,3'-bis(2,4,6-triisopropylphenyl)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 629645-69-8 3,3'-bis(2,6-diisopropylphenyl)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 35193-70-5 2-hydroxy-2'-methoxy-1,1'-binaphthyl 
• 484023-88-3 ethyl (RS)-3-[3'-iodo-2,2'-dimethoxy-1,1'-binaphth-3-yl]-2-[(diphenylmethylene)amino]propanoate 

Relevant academic research and scientific papers

Zirconium-redox-shuttled cross-electrophile coupling of aromatic and heteroaromatic halides

Transition metal-catalyzed cross-electrophile coupling (XEC) is a powerful tool for forging C(sp2)–C(sp2) bonds in biaryl molecules from abundant aromatic halides. While the synthesis of unsymmetrical biaryl compounds through multimetallic XEC is of high synthetic value, the selective XEC of two heteroaromatic halides remains elusive and challenging. Herein, we report a homogeneous XEC method, which relies on a zirconaaziridine complex as a shuttle for dual palladium-catalyzed processes. The zirconaaziridine-mediated palladium (ZAPd)-catalyzed reaction shows excellent compatibility with various functional groups and diverse heteroaromatic scaffolds. In accord with density functional theory (DFT) calculations, a redox transmetallation between the oxidative addition product and the zirconaaziridine is proposed as the crucial elementary step. Thus, cross-coupling selectivity using a single transition metal catalyst is controlled by the relative rate of oxidative addition of Pd(0) into the aromatic halide. Overall, the concept of a combined reducing and transmetallating agent offers opportunities for the development of transition metal reductive coupling catalysis.

Palladium nanoparticle catalysis: Borylation of aryl and benzyl halides and one-pot biaryl synthesis via sequential borylation-Suzuki-Miyaura coupling

Palladium nanoparticles generated in PEG catalyze the reaction of bis(pinacolato)diboron with various aryl/benzyl halides to afford aryl/benzyl boronates in high yield. Arylboronates thus prepared, have been directly used in the Suzuki-Miyaura coupling reaction with different aryl halides and benzyl halides in a convenient one-pot, two-step solvent free green synthesis of unsymmetrical biaryls and diarylmethanes. The Royal Society of Chemistry 2012.

Ferrocenyl phosphine-oxazaphospholidine oxide ligands for the Suzuki-Miyaura coupling of hindered aryl bromides and chlorides

A series of ferrocenyl oxazaphospholidine phosphines that differ electronically and sterically were investigated as ligands for the Suzuki-Miyaura cross-coupling reactions. One of these compounds, 1, was shown to be highly effective in the coupling reactions of bulky aryl bromides with boronic acids when combined with Pd(OAc)2, while another, 2, was capable of coupling aryl chlorides with boronic acids. However, these ligands were less effective in asymmetric induction.

Regioselective Halogenation and Dimerization of Alkoxynaphathalenes with Alumina- or Kieselguhr-supported Copper(II) Halides

The reaction of 1-alkoxynaphathalenes 1 with alumina-supported copper(II) bromide or copper(II) chloride gave dimers, 4,4'-dialkoxy-1,1'-binaphthyls 3, as major products, and with Kieselguhr-supported copper(II) bromide afforded 1-bromo-4-alkoxynaphthalenes 2, while the reaction of 2-alkoxynaphathalenes 4 with alumina- or Kieselguhr-supported copper(II) bromide gave preferentially 1-bromo-2-alkoxynaphthalenes 5.

Spontaneous Resolution of 2,2'-Dimethoxy-1,1'-binaphthalene

The dimethyl ether of 1,1'-bi-2-naphthol crystallizes as a conglomerate and can be resolved without chiral auxiliaries by entrainment.The direct crystallization of a supersaturated solution of the title compound partially enriched by one enantiomer (ee ca. 2percent) is conducted in anisole at 40 deg C and gives, after one crystallization, a compound with ee >98percent.Demethylation under nonracemizing conditions gives the enantiomeric 1,1'-bi-2-naphthol.

Pd(0)-CATALYZED ELECTRO-REDUCTIVE COUPLING OF ARYL HALIDES

An efficient electro-reductive coupling of aryl bromides and iodides into biaryls has been performed by the electrolysis with Pd(0)- and/or Pd(II)-catalysts in a DMF-Et4NOTs-(Pb cathode) system. 4-Bromo- and 2-bromopyridines were also converted into the corresponding bipyridyls, respectively.