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Upstream product

• 586-77-6 4-bromo-N,N-dimethylaniline 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 91430-31-8 C₁₁H₁₆N₂O₂ 
• 1197-19-9 4-cyano-N,N-dimethylaniline 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 619-84-1 p-N,N-dimethylaminobenzoic acid 
• 698-70-4 4-Iodo-N,N-dimethylaniline 
• 403-46-3 4-fluoro-N,N-dimethylaniline 

Downstream Products

• 1202-25-1 methyl 4-(N,N-dimethylamino)benzoate 
• 619-84-1 p-N,N-dimethylaminobenzoic acid 
• 359653-43-3 2-(4-N,N-dimethylaminophenyl)naphthalene 
• 1060639-09-9 1,4,5,8-tetrakis[4-(dimethylamino)phenyl]-9,10-anthracenedione 
• 1192464-36-0 N,N'-bis(1-ethylpropyl)-2,5,8,11-tetrakis[p-(N,N-dimethylamino)phenyl]perylene-3,4:9,10-tetracarboxylic acid bisimide 
• 1234421-77-2 N,N-dimethyl-2'-(pyridin-2-yl)-[1,1'-biphenyl]-4-amine 
• 1174895-53-4 2-(4′-(trifluoromethyl)-[1,1′-biphenyl]-2-yl)pyridine 
• 1426442-22-9 C₂₅H₂₃N 
• 1426442-23-0 N,N-dimethyl-4-((S)-(naphthalene-2-yl)(phenyl)methyl)benzenamine 
• 1426442-39-8 C₂₇H₂₅N 
• 1415045-40-7 N,N-diethyl-2-(4-(dimethylamino)phenyl)furan-3-carboxamide 

Relevant academic research and scientific papers

Ni-Catalyzed Borylation of Aryl Sulfoxides

A nickel/N-heterocyclic carbene (NHC) catalytic system has been developed for the borylation of aryl sulfoxides with B2(neop)2 (neop=neopentyl glycolato). A wide range of aryl sulfoxides with different electronic and steric properties were converted into the corresponding arylboronic esters in good yields. The regioselective borylation of unsymmetric diaryl sulfoxides was also feasible leading to borylation of the sterically less encumbered aryl substituent. Competition experiments demonstrated that an electron-deficient aryl moiety reacts preferentially. The origin of the selectivity in the Ni-catalyzed borylation of electronically biased unsymmetrical diaryl sulfoxide lies in the oxidative addition step of the catalytic cycle, as oxidative addition of methoxyphenyl 4-(trifluoromethyl)phenyl sulfoxide to the Ni(0) complex occurs selectively to give the structurally characterized complex trans-[Ni(ICy)2(4-CF3-C6H4){(SO)-4-MeO-C6H4}] 4. For complex 5, the isomer trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I was structurally characterized in which the phenyl sulfinyl ligand is bound via the oxygen atom to nickel. In solution, the complex trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I is in equilibrium with the S-bonded isomer trans-[Ni(ICy)2(C6H5)(SOC6H5)] 5, as shown by NMR spectroscopy. DFT calculations reveal that these isomers are separated by a mere 0.3 kJ/mol (M06/def2-TZVP-level of theory) and connected via a transition state trans-[Ni(ICy)2(C6H5)(η2-{SO}-C6H5)], which lies only 10.8 kcal/mol above 5.

Nickel-Catalyzed Decarbonylative Borylation of Amides: Evidence for Acyl C?N Bond Activation

A nickel/N-heterocyclic carbene catalytic system has been established for decarbonylative borylation of amides with B2nep2by C?N bond activation. This transformation shows good functional-group compatibility and can serve as a powerful synthetic tool for late-stage borylation of amide groups in complex compounds. More importantly, as a key intermediate, the structure of an acyl nickel complex was first confirmed by X-ray analysis. Furthermore, the decarbonylative process was also observed. These findings confirm the key mechanistic features of the acyl C?N bond activation process.

Ni-Catalyzed Borylation of Aryl Fluorides via C-F Cleavage

A Ni-catalyzed borylation via C-F activation is described. This protocol is distinguished by a wide scope, including unactivated fluoroarenes, without compromising its efficiency and scalability, thus representing a significant step-forward toward the implementation of C-F activation protocols.

PROCESS FOR THE BORYLATION OF ORGANOHALIDES

The present invention relates to a process for the borylation of organohalides.

Rhodium(I)-catalyzed borylation of nitriles through the cleavage of carbon-cyano bonds

The reaction of aryl cyanides with diboron in the presence of a rhodium/Xantphos catalyst and DABCO affords arylboronic esters via carbon-cyano bond cleavage. This unprecedented mode of reactivity for a borylrhodium species allows the regioselective intro

Borylation of organo halides and triflates using tetrakis(dimethylamino) diboron

We report a new in situ borylation method using tetrakis(dimethylamino) diboron, DMA4B2, in the presence of a diol. Our method uses standard borylation conditions and readily available Pd-catalysts. The scope of this method includes aryl halides and triflates as well as vinyl halides and triflates. The method successfully works with a broad range of diols, enabling the selection of the best boronic ester for subsequent Suzuki coupling.

Borylation of aryl and alkenyl carbamates through Ni-catalyzed C-O activation

Direct borylation of aryl/alkenyl carbamates was developed through Ni catalysis. A broad substrate scope, including aryl, alkenyl, and heterocyclic derivatives, was studied. This study offers a convenient method to approach aryl/alkenyl boronic esters from phenol and ketone derivatives (see scheme). Copyright