Azidosubstituted arylboronic acids: Synthesis and Suzuki-Miyaura cross-coupling reactions

Article abstract of DOI:10.1016/j.tet.2005.12.026

Arylboronic acids having a remote azido group were prepared from the corresponding azidosubstituted aryl bromides via lithiation and treatment with trialkyl borates. Preparative yields were achieved when the starting aryl bromides possessed ortho-alkoxy groups, which would stabilize the intermediate aryllithium species. Conventional Suzuki cross-coupling of the arylboronic acids proceeded generally well with retention of azido group; however, sometimes azidomethyl fragment underwent oxidative transformation into a nitrile.