7519-92-8

Upstream product

• 7637-07-2 boron trifluoride 
• 36229-42-2 (3-chlorophenyl)magnesium bromide 
• 121-43-7 Trimethyl borate 
• 63503-60-6 3-chlorophenylboronic acid 

Downstream Products

• 18733-76-1 (2-Cl-C₆H₄)2Si{OB(C₆H₄-3-Cl)}2O 
• 1224738-36-6 N-benzyl-4-(3-chlorophenyl)-3,4-dihydroquinolin-2(1H)-one 
• 1313872-36-4 N-[3-(3-chlorophenyl)oxetan-3-yl]-2-methylpropane-2-sulfinamide 
• 1313872-67-1 C₃₇H₃₃ClN₂O₂S 
• 1313872-57-9 C₁₈H₂₇ClN₂O₃S 
• 41605-90-7 1-(3-chlorophenyl)morpholine 
• 89170-76-3 N,N-dibenzyl-3-chlorobenzenamine 
• 1255949-82-6 C₁₄H₂₀ClO₅P 

Relevant academic research and scientific papers

Palladium(II)-Catalyzed Enantioselective Synthesis of α-(Trifluoromethyl)arylmethylamines

We describe a method for the synthesis of α-(trifluoromethyl)arylmethylamines that consists of the palladium(II)-catalyzed addition of arylboroxines to imines derived from trifluoroacetaldehyde. Palladium acetate is used as a catalyst with electron-neutral or electron-rich arylboroxines, and it was found that addition of an ammonium or silver salt was crucial to promote the reaction of electron-poor boroxines. With (S)-t-Bu-PyOX as the chiral ligand, this method delivers a variety of α-trifluoromethylated amines in 57-91% yield and with greater than 92% ee in most cases.

Oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles: The enolate chan–evans–lam reaction

Reported is a versatile new oxidative method for the arylation of activated methylene species. Under mild reaction conditions (RT to 40°C), Cu(OTf)2mediates the selective coupling of functionalized aryl boron species with a variety of stabilized sp3-nucleophiles. Tertiary malonates and amido esters can be employed as substrates to generate quaternary centers. Complementing either traditional cross-coupling or SNAr protocols, the transformation is chemoselective in the presence of halogen electrophiles, including aryl bromides and iodides. Substrates bearing amide, sulfonyl, and phosphonyl groups, which are not amenable to coupling under mild Hurtley-type conditions, are suitable reaction partners.

Oxidative Heck desymmetrisation of 2,2-disubstituted cyclopentene-1,3-diones

Oxidative Heck couplings have been successfully developed for 2,2-disubstituted cyclopentene-1,3-diones. The direct coupling onto the 2,2-disubstituted cyclopentene-1,3-dione core provides a novel expedient way of enantioselectively desymmetrising all-carbon quaternary centres. This journal is

Diastereoselective synthesis of vicinally bis(trifluoromethylated) alkylboron compounds through successive insertions of 2,2,2-trifluorodiazoethane

The usefulness of embedded CF3 substituents within organic substructures necessitates the development of diverse methods for incorporating this functional group. A recently reported route to α-trifluoromethylated alkylboron compounds by an α-transfer mechanism has now been extended to the synthesis of unprecedented, vicinally ditrifluoromethylated alkylboron compounds in a diastereoselective fashion. The utility of these products is highlighted by conversion of the C-B bond into other functional groups.

Scalable synthesis of oxazolones from propargylic alcohols through multistep palladium(II) catalysis: β-selective oxidative heck coupling of cyclic sulfonyl enamides and aryl boroxines

A whale of a scale: The title oxidative Heck coupling proceeded with unusual β selectivity to generate a variety of branched substituted oxazolones (see scheme; Ts=p-toluenesulfonyl). The three-step synthesis from readily available starting materials with a simple palladium catalyst and inexpensive reagents could be carried out in a single reaction vessel or scaled up for the preparation of large amounts of these amino acid precursors. Copyright

Transition-metal-free electrophilic amination of arylboroxines

A transition-metal-free strategy to construct C(sp2)-N bonds using arylboroxines and O-benzoyl hydroxylamines as coupling partners has been developed. This transformation provides a useful method to access various aromatic amines.

Mild and ligand-free Pd(II)-catalyzed conjugate additions to hindered γ-substituted cyclohexenones

Ligand-free cationic Pd(II) catalyst with NaNO3 as an additive is a highly active catalytic system for conjugate additions to sterically hindered γ-substituted cyclohexenones. More challenging γγ- and βγ-substrates also react well to produce products with quaternary centers in good dr. The conjugate additions occur in a diastereoselective fashion under mild, practical and air-stable conditions, using readily available commercial reagents.

Rh-catalyzed addition of arylboroxines to cyclic N -(Isopropanesulfinyl) ketimines

Arylboroxines, which are easily accessed by drying commercially available arylboronic acids, are added to N-(isopropanesulfinyl)ketimines derived from cyclohexanone, N-Boc-piperidin-4-one, and tetrahydropyran-4-one in high yields and with excellent functional group compatibility via rhodium catalysis. These results contrast with additions to the corresponding ketimines incorporating the larger N-tert-butanesulfinyl group, which give considerably lower yields. Efficient two-step preparation of racemic isopropanesulfinamide from inexpensive isopropyl disulfide and recycling of the isopropanesulfinyl group from the addition products are also described.

Rh-catalyzed addition of arylboroxines to cyclic N -(Isopropanesulfinyl) ketimines

Arylboroxines, which are easily accessed by drying commercially available arylboronic acids, are added to N-(isopropanesulfinyl)ketimines derived from cyclohexanone, N-Boc-piperidin-4-one, and tetrahydropyran-4-one in high yields and with excellent functional group compatibility via rhodium catalysis. These results contrast with additions to the corresponding ketimines incorporating the larger N-tert-butanesulfinyl group, which give considerably lower yields. Efficient two-step preparation of racemic isopropanesulfinamide from inexpensive isopropyl disulfide and recycling of the isopropanesulfinyl group from the addition products are also described.

Palladium-catalyzed cascade reaction for the synthesis of substituted isoindolines

Arylate then cyclize: A palladium(II)-catalyzed cascade sequence has been developed to provide highly diastereomerically enriched cis-1-aryl-3-vinyl isoindolines (see scheme). The method uses commercially available aryl boronic acids and boroxine compounds containing a variety of electron-rich, -neutral, or -poor aromatic groups. Ts=4-toluenesulfonyl. Copyright