Allylation of aldehydes by allyl alcohols via palladium pincer complex catalyzed formation of transient allylboronic acids

ORGN 143

Nicklas Selander, nicklas@organ.su.se, Sara Sebelius, sara@organ.su.se, Vilhelm J. Olsson, ville@organ.su.se, and Kalman J. Szabo, kalman@organ.su.se. Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory, Stockholm, SE-10691, Sweden
Highly regio- and stereoselective coupling of allyl alcohols (e.g. 1) with aldehydes (e.g. 2) can be achieved with SeCSe pincer complex catalyst (4) and p-toluenesulfonic acid (5) in the presence of diboronic acid (3). The reactions could be performed as an operationally simple one-pot sequence. The transformations have a very broad synthetic scope and the high yields were obtained without use of an inert atmosphere and dried solvents. Results for allylation of other electrophiles (in place of aldehydes) will also presented.

 

Process R&D, Physical Organic Chemistry, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, March 25, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Sci-Mix

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007