An Efficient Ni/Pd Catalyzed Chemoselective Synthesis of 1,3,2-Benzodiazaborininones from Boronic Acids and Anthranilamides
An efficient Ni/Pd catalyzed chemoselective synthesis of 1,3,2-benzodiazaborininones from boronic acids and anthranilamide has been developed. This protocol allows for the rapid and straightforward access to a wide range of 1,3,2-benzodiazaborininones at roomtemperature with excellent functional group tolerance. (Figure presented.).
Anthranilamide (aam)-substituted diboron: palladium-catalyzed selective B(aam) transfer
An unsymmetrical diboron bearing an anthranilamide (aam) substituent was synthesized and was found to be coupled with aryl halides through the palladium-catalyzed Miyaura-Ishiyama-type reaction. The selective transfer of aam-substituted boryl moiety led t
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.