Synthesis of Trimethylstannyl Arylboronate Compounds by Sandmeyer-type Transformations and Their Applications in Chemoselective Cross-Coupling Reactions

J Org Chem. 2014 Mar 7;79(5):1979-88. doi: 10.1021/jo402618r. Epub 2014 Feb 20.

Abstract

A synthetic method based on Sandmeyer-type reactions to access both tin- and boron-substituted arenes from nitroaniline derivatives is described. This transformation can be applied to the synthesis of a series of functionalized trimethylstannyl arylboronates. In addition, the chemoselective reaction of the Stille and Suzuki-Miyaura cross-coupling reactions is explored, and a series of m- and p-terphenyl derivatives have been synthesized by conducting consecutive one-pot Stille and Suzuki-Miyaura cross-coupling reactions.