1315331-06-6

Upstream product

• 28144-70-9 anthranilic acid amide 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 1296939-26-8 2-(3-bromophenyl)-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 1296939-43-9 2-{4-(dimethylphenylsilyl)-4'-methyl-[1,1'-biphenyl]-3-yl}-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one 
• 1449074-49-0 C₂₀H₁₆BIN₂O 

Relevant academic research and scientific papers

Anthranilamide-masked o-iodoarylboronic acids as coupling modules for iterative synthesis of ortho-linked oligoarenes

Anthranilamide (AAM)-masked o-iodoarylboronic acids were prepared from AAM-masked arylboronic acids via Rucatalyzed o-C-H silylation, followed by iododesilylation with ICl. The Suzuki-Miyaura coupling of AAM-masked o-haloarylboronic acids with arylboronic acids proceeded under ligandfree conditions. Oligo(o-phenylene)s and oligo(naphthalene-2,3-diyl)s were synthesized via iterative Suzuki-Miyaura coupling sequences.

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.