Conjugate additions of aryl boronic acids to electron-deficient olefins

ORGN 500

William C. Trenkle, trenkle@Brown.edu, Marcus D. Faust Jr., Julia L. Barkin, and Dwight A. Sweigart, Dwight_Sweigart@Brown.edu. Department of Chemistry, Brown University, Box H, Providence, RI 02912
The conjugate addition of aryl boronic acids to unsaturated carbonyl compounds remains one of the most versatile methods for the formation of carbon-carbon bonds. Herein we report the development of a mild set of conditions using a new rhodium catalyst in aqueous media, which is effective for a wide range of sterically hindered substrates. These conditions utilize low levels of catalyst loading (0.5 mol% to 1.0 mol %) and boronic acid (1.2 to 2 equivalents relative to olefin) to produce the desired 1, 4 conjugate addition products. Studies to elucidate the scope and versatility of this system will be described.

 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006