1160553-91-2

Upstream product

• 98-80-6 phenylboronic acid 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1296939-27-9 2-[2-(dimethylphenylsilyl)phenyl]-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one 
• 1160553-79-6 C₆H₄B(N₃HC₉H₆)Si(CH₃)2C₆H₅ 

Relevant academic research and scientific papers

Anthranilamide: A simple, removable ortho -directing modifier for arylboronic acids serving also as a protecting group in cross-coupling Reactions

Anthranilamide (AAM) serves as a bifunctional modifier on the boron atom in catalytic transformations of arylboronic acids. It makes boronyl groups unreactive in Suzuki-Miyaura coupling and promotes Ru-catalyzed ortho-silylation. Suzuki-Miyaura coupling of AAM-modified bromophenylboronic acids with tolylboronic acid gave 1,1′-biaryl-4-boronic acid bearing AAM on the boron atom, which subsequently underwent Ru-catalyzed ortho-silylation at the 3-position by virtue of the ortho-directing effect of the AAM group.

Easily attachable and detachable ortho-directing agent for arylboronic acids in ruthenium-catalyzed aromatic C-H silylation

(Chemical Equation Presented) o-C?H silylation of arylboronic acids has been achieved using 2-pyrazol-5-ylaniline as an orthodirecting agent, which was temporarily attached to the boronyl group via Ru-catalyzed silylation with hydrosilanes. Condensation products of arylboronic acids with2-pyrazol-5-ylaniline were prepared in situ and subjected to reaction w ith triorganosilanes in the presence of RuH2(CO)(PPh3) 3 at 135°C. Regioselective silylation at their ortho-positions proceeded in good yields for phenylboronic acids bearing para-substituents such as chloro, fluoro, methyl, methoxy, and trifluoromethyl groups. p-Methoxycarbonyl-substituted phenylboronic acid provided thecorresponding silylated product in moderate yield. m-Tolyl- and 2-napht hylboronic acids underwent silylation selectively at the less stericallyhindered ortho-positions. The silylated products were utilized in Suzuk i?Miyaura coupling, followed either by iodination with ICl or by Tamao oxidation to furnish iodine- or hydroxy-substituted biaryls.