Application of a Diels-Alder approach to biaryls and a novel boroxine-based Suzuki coupling strategy in the synthesis and functionalization of tetra-ortho substituted biaryl templates

ORGN 524

Johanna R. Perkins, perkinjo@science.orst.edu and Rich G. Carter, rich.carter@oregonstate.edu. Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR 97333
Biaryl-containing compounds have become a prominent class in the synthetic, biological, and chemical communities due to their unique structural characteristics. Our laboratory has developed a novel Diels-Alder based approach to biaryls (DAB), which provides access to a wide range of functional group combinations that are not readily available through more traditional methods. The application of this strategy to a series of tetra-ortho-substituted, stannane-containing biaryl compounds possessing complete orthogonal functionality will be presented. Additionally, the development of a palladium-catalyzed cross coupling strategy involving boroxines with unique and powerful reactivity will be disclosed.

 

New Reactions and Methodology
8:00 AM-11:40 AM, Wednesday, August 20, 2008 Pennsylvania Convention Center -- 203 A&B, Oral

Division of Organic Chemistry

The 236th ACS National Meeting, Philadelphia, PA, August 17-21, 2008