150766-94-2

Upstream product

• 578-57-4 2-bromoanisole 
• 7440-66-6 zinc 
• 529-28-2 4-iodoanisol 
• 31600-86-9 2-methoxyphenyllithium 
• 100-66-3 methoxybenzene 
• 7699-45-8 zinc dibromide 
• 16750-63-3 2-methoxyphenylmagnesium bromide 

Downstream Products

• 5181-06-6 1-(2-methoxy-phenyl)piperidine 
• 4877-93-4 2,2'-Dimethoxybiphenyl 
• 65570-20-9 butyl-(2-methoxy-phenyl)amine 
• 2553-04-0 ortho-methoxybenzophenone 
• 61578-10-7 (2-methoxy-phenyl)-(piperidin-1-yl)methanone 
• 13102-33-5 2,2'-dimethoxybenzophenone 

Relevant academic research and scientific papers

Stereostructure and thermodynamic stability of atropisomers of ortho-substituted 2,2′-diaryl-1,1′-binaphthalenes

A series of ortho-substituted 2,2′-aryl-1,1′-binaphthalenes were prepared via Negishi arylation of 2,2′-diiodo-1,1′- binaphthalene in good to high yields (65-95%) as an equilibrium mixtures of up to three atropisomers (unlike,unlike, like,unlike, and like,like). Thermodynamic stability parameters of the atropisomers were evaluated from VT NMR spectra by regression analysis. The DFT parameters calculated using CAM-B3LYP functional comprising solvent permittivity were, apart from the toluene solution, which was expected to interact with the aromatic solute, in qualitative agreement with the experimental values. In the case of the ditolyl derivative, the population of the atropisomers was confirmed by CD spectroscopy via comparison with the population-weighted averaged spectrum computed using the M06 functional. X-ray structure analyses of particular atropisomers of the dianisyl, dianilinyl, and dinaphthyl derivatives are also presented and discussed.

Sequential Organozinc Formation and Negishi Cross-Coupling of Amides Catalysed by Cobalt Salt

Herein, a cobalt-catalysed Negishi-type cross-coupling of amide derivatives is described. Apart from being the first example of cobalt-catalysed Negishi-type coupling of amides, the process described employs a unique, simple, and cheap catalytic system to perform both the organozinc formation and the Negishi-type coupling. Indeed, the same cobalt(II) bromide salt used to form the arylzinc species from aryl bromides is then re-used to perform the cross coupling of this resulting arylzinc with N-benzoyl glutarimides at room temperature. The main advantages of the reaction presented are its robustness and ease of use. Indeed, the reactions of organozinc formation and Negishi-type coupling are performed without precautions toward water or oxygen. (Figure presented.).

Cobalt-Catalyzed Oxidative Homocoupling of Arylzinc Species

A novel procedure for the synthesis of functionalized symmetrical biaryl compounds is described. The reaction proceeds via the oxidative homocoupling of arylzinc species formed by cobalt catalysis in the presence of air or p-benzoquinone depending on the nature of the functional group.

Synthesis of Symmetrical Diaryl Ketones by Cobalt-Catalyzed Reaction of Arylzinc Reagents with Ethyl Chloroformate

Symmetrical diaryl ketones were prepared by a cross-coupling reaction between aryl bromides and ethyl chloroformate. This new method, which uses a catalyst composed of CoBr2and a bipyridine ligand along with readily available starting materials, allows for the synthesis of a variety of symmetrical diaryl ketones in moderate to excellent yields (37–99 %) under mild conditions. This reaction, in which ethyl chloroformate acts as a surrogate of carbon monoxide in the presence of cobalt and zinc, represents an interesting alternative to previously known approaches for the synthesis of diarylmethanones.

α-C-Glycosides via syn Opening of 1,2-Anhydro Sugars with Organozinc Compounds in Toluene/n-Dibutyl Ether

The diastereoselective addition of organozinc species to 1,2-anhydro sugars in toluene/n-dibutyl ether solvent is reported. Compared to the existing methods, the reaction proceeds at 0 °C, and only a slight excess of nucleophile is required to achieve good yields. Scope was assessed with different O-protected glycals along with various nucleophiles (aryl, alkynyl). This methodology was applied to the synthesis of the α-anomer of canagliflozin.

Highly sterically hindered binaphthalene-based monophosphane ligands: Synthesis and application in stereoselective Suzuki-Miyaura reactions

A series of new sterically hindered (R)-(2′-aryl-1,1′- binaphthalene-2-yl)phosphanes with ortho-substituted phenyls as aryl groups were prepared via Negishi monoarylation of enantiopure 2,2′-dibromo-1, 1′-binaphthalene followed by lithiation and quenching with diphenylphosphanyl or dicyclohexylphosphanyl chloride. These ligands were applied to the stereoselective Suzuki-Miyaura coupling for the preparation of substituted biaryls. The enantioselectivity correlated positively when increasing the hindrance of the 2′-aryl group of the ligand. Using the best performing diphenylphosphane ligand with a 2,6-dimethoxyphenyl aryl group, various arylnaphthalenes were prepared in high to excellent yields (68-99%) with low to good ee (12-75% ee), the latter being comparable to the best values reported when using other chiral monophosphane ligands.

Cobalt-catalyzed electrophilic amination of arylzincs with N-chloroamines

Roles reversed: An efficient cobalt-catalyzed electrophilic amination of arylzinc reagents has been achieved. A variety of functionalized arylzincs and N-chloroamines were coupled under mild conditions (see scheme). Both secondary and tertiary arylamines were obtained in moderate to excellent yields. Copyright

Cobalt-catalyzed addition of arylzinc reagents to alkynes to form ortho-alkenylarylzinc species through 1,4-cobalt migration

Migratory carbometalation: A cobalt-Xantphos complex catalyzes the addition of an arylzinc reagent to an unactivated internal alkyne; the reaction most likely involves insertion of the alkyne into an arylcobalt species and vinyl-to-aryl 1,4-cobalt migration, followed by transmetalation with the arylzinc reagent. Interception of the resulting ortho-alkenylarylzinc species with electrophiles allows access to 1-alkenyl arenes functionalized in the 2-position. Copyright

New chemical synthesis of functionalized arylzinc compounds from aromatic or thienyl bromides under mild conditions using a simple cobalt catalyst and zinc dust

A new chemical method for the preparation of arylzinc intermediates is described in acetonitrile, on the basis of the activation of aryl bromides by low-valent cobalt species arising from the reduction of cobalt halide by zinc dust. This procedure allows for the synthesis of a variety of functionalized aryl- and thienylzinc species in good to excellent yields. The versatility and the simplicity of that original method represent an alternative to most known procedures.