1296939-27-9

Upstream product

• 98-80-6 phenylboronic acid 
• 28144-70-9 anthranilic acid amide 
• 28249-75-4 2-phenyl-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one 
• 766-77-8 Dimethylphenylsilane 

Downstream Products

• 1296939-41-7 2,4,6-tris[2-(dimethylphenylsilyl)phenyl]boroxine 
• 1160553-91-2 1-dimethylphenylsilyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene 
• 1449074-42-3 C₁₃H₁₀BIN₂O 

Relevant academic research and scientific papers

Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation

A new, operationally simple approach is presented to access arynes and their fluoride-activated precursors based on Ru-catalyzed C-H silylation of arylboronates. Chromatographic purification may be deferred until after aryne capture, rendering the arylboronates de facto precursors. Access to various new arynes and their derivatives is demonstrated, including, for the first time, those based on a 2,3-carbazolyne and 2,3-fluorenyne core, which pave the way for novel derivatizations of motifs relevant to materials chemistry.

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.