How does the non-transferable group on the triorganotin species affect the rate of the Stille reaction?

ORGN 203

Robert E. Maleczka Jr., maleczka@cem.msu.edu and Nicole M. Torres, torresn2@msu.edu. Department of Chemistry, Michigan State University, 540 Chemistry, East Lansing, MI 48824
Prior studies on the mechanism of the Stille reaction have shown the transmetalation step as rate determining for sp2 organohalides. Surprisingly, no systematic studies have been performed to ascertain the relative rates of reaction per various non-transferable ligands on tin. This information would prove useful when determining which tin species to employ in the Stille reaction. Sn119 NMR was utilized to monitor the course of the Stille reaction. The relative coupling rates of trimethyl, tributyl, and other triorganotin species were determined from reactions with various organohalide electrophiles under traditional and modified Stille conditions. These data will be presented.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

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