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

作者：Sviridov SI; Vasi'ev AA^*; Sergovskaya NL; Chirskaya MV; Shorshnev SV

来源：Tetrahedron, 2006, 62(11): 2639-2647.

DOI：10.1016/j.tet.2005.12.026

• azides
• boronic acids
• cross-coupling
• 2,3-dihydrobenzo[b]lfurans
• nitriles

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.

• 出版日期2006-3-13