Microwave technologies are being employed to increase yields and decrease reaction times for many reactions. For both brominated and iodinated substrates, we have observed higher yields for microwave Suzuki-Miyaura cross-couplings using cesium carbonate rather than sodium carbonate as the base; however, this increase in product yield was not observed for all substrates and it is of interest to determine if functional group placement with respect to the halogen has an effect on the product yield difference resulting from changing the cation from sodium to cesium.  Additionally, we are evaluating the cesium effect using traditional heating methods to determine whether the observed effect is due to the microwave or an inherent factor of the reaction.  Finally, in an effort to determine the role of the alkaline base, molecular modeling is being performed using Hartree-Fock 6-31G* quantum calculations in Spartan.  The primary goal of this research is to learn more about the role of the cation in the Suzuki-Miyaura cross-coupling mechanism.

Evaluating the role of the cation in the Suzuki-Miyaura cross-coupling mechanism

246th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.