Anthranilamide: A Simple, Removable ortho-Directing Modifier for Arylboronic Acids Serving also as a Protecting Group in Cross-Coupling Reactions

作者：Ihara Hideki; Koyanagi Masashi; Suginome Michinori^*

来源：Organic Letters, 2011, 13(10): 2662-2665.

DOI：10.1021/ol200764g

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.

• 出版日期2011-5-20