79421-98-0

Upstream product

• 17933-03-8 m-tolylboronic acid 
• 7637-07-2 boron trifluoride 
• 28987-79-3 m-tolylmagnesium bromide 
• 688-74-4 boric acid tributyl ester 

Downstream Products

• 36821-15-5 2-(3-methylphenyl)naphthalene 
• 1133798-31-8 methyl 2-m-tolyl-2-p-tolylacetate 
• 4333-70-4 1-(phenyl)-1-(m-tolyl)ethylene 
• 137474-24-9 3-methylbenzhydrol 
• 1309579-51-8 2-methyl-4-[2-(3-methylphenyl)ethyl]pyridine 
• 87199-16-4 3-Formylphenylboronic acid 
• 1313872-32-0 C₁₄H₂₁NO₂S 
• 1338045-65-0 C₂₁H₂₆O₅ 
• 1354729-08-0 C₂₄H₂₄O 
• 1365284-30-5 C₂₁H₁₉NO₂S 
• 1365284-08-7 (R)-3-phenyl-3-(m-tolyl)-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide 
• 6922-90-3 (3-methylphenyl)(diphenyl)methanol 
• 1362132-00-0 (R)-1-phenyl-1-m-tolylpropan-1-ol 
• 1362132-08-8 (R)-1-m-tolyl-1,2,3,4-tetrahydronaphthalen-1-ol 

Relevant academic research and scientific papers

Ni-Catalyzed Intermolecular Carboacylation of Internal Alkynes via Amide C-N Bond Activation

The Ni-catalyzed carboacylation of alkynes with amide electrophiles and triarylboroxines is presented. The reaction generates all-carbon tetrasubstituted alkene products in up to 62% yield. NiCl2·glyme is used as an inexpensive precatalyst in the absence

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.

Asymmetric Synthesis of Triarylmethanes by Rhodium-Catalyzed Enantioselective Arylation of Diarylmethylamines with Arylboroxines

The reaction of racemic diarylmethylamines, (Ar1Ar2CHNR2), where Ar1 is substituted with a 2-hydroxy group, with arylboroxines (Ar3BO)3 in the presence of a chiral diene-rhodium catalyst gave high yields of chiral triarylmethanes (Ar1Ar2CH?Ar3) with high enantioselectivity (up to 97% ee). The reaction is assumed to proceed through o-quinone methide intermediates which undergo Rh-catalyzed asymmetric 1,4-addition of the arylboron reagents.

Enantioselective, nickel-catalyzed suzuki cross-coupling of quinolinium ions

Quinolinium ions are engaged in an asymmetric, Ni-catalyzed Suzuki cross-coupling to yield 2-aryl- and 2-heteroaryl-1,2-dihydroquinolines. Key to the development of this method is the use of a Ni(II) precatalyst that activates without the need for strong reductants or high temperatures. The Ni-iminium activation mode is demonstrated as an exceptionally mild pathway to generate enantioenriched products from racemic starting materials.

Rhodium-catalyzed asymmetric hydroarylation of 3-pyrrolines giving 3-arylpyrrolidines: Protonation as a key step

A hydroxorhodium complex coordinated with (R)-segphos was found to catalyze the hydroarylation of 3-pyrrolines with arylboroxines under neutral conditions to give 3-arylpyrrolidines with high enantioselectivity in high yields.

Palladium(II)-catalyzed enantioselective synthesis of α- (trifluoromethyl)arylmethylamines

Trifluoromethylacetaldimines, generated in situ from the corresponding N,O-acetals, undergo 1,2-addition of arylboroxines under palladium(II) catalysis to generate a variety of α-(trifluoromethyl)arylmethylamines with good to high enantioselectivity (up to 97% ee). The pyridine-oxazolidine (PyOX) class of ligands was found to be particularly suitable for this transformation, which proceeds without exclusion of ambient air and moisture.

Rhodium(I)/diene-catalyzed addition reactions of arylborons with ketones

Rh(I)/diene-catalyzed addition reactions of arylboroxines/arylboronic acids with unactivated ketones to form tertiary alcohols in good to excellent yields are described. By using C2-symmetric (3aR,6aR)-3,6-diaryl-1,3a,4,6a- tetrahydropentalenes as ligands, the asymmetric version of such an addition reaction, with up to 68% ee, was also realized.

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.