Metal Catalyzed Methods for the Preparation of Organosilanes and Related Molecules

With the support of the Chemical Synthesis (SYN) program in the Division of Chemistry, Donald A. Watson of the University of Delaware is studying the new catalytic methods to prepare organic molecules that contain silicon atoms. Such molecules, commonly called organosilanes, are important building blocks for the complex organic chemical compounds that are used as pharmaceuticals, as agrochemicals, and for the study of biology.

This research aims to develop new reactions that allow for these important silicon containing compounds to be prepared in new, straightforward ways using inexpensive starting materials and catalytic amounts of reaction promoters. Not only will this research expand access to organosilanes, but it will also increase fundamental understanding of the reactions silicon containing molecules and their interactions with transition metal catalysts.

The program will also train undergraduate student, graduate student and post-doctoral researchers, and will build outreach programs to both early childhood education and undergraduate-only higher educations institutions that lack advanced research technology. In so doing, the research program will seek to train the next generation of chemical scientist who will tackle the challenges of tomorrow.

The focus of the research program is the development of new cross-coupling reactions of electrophilic silanes. Using transition metal catalysts, Dr. Donald Watson and his students seek to develop new methods for C-Si bond construction to prepare a variety of both saturated and unsaturated organosilanes via cross-coupling with simple organic nucleophiles.

To achieve this result, the Watson group has designed a new type of silyl-Heck reaction with analogy to the robust and highly studied parent Heck reaction of alkenes. This newer silyl variant of the Heck coupling is expected to permit access to otherwise challenging vinylic and allylic silane targets. The Watson team then seeks to develop related multi-component transformations to access even more complex and highly substituted alkylsilanes.

In parallel to the development of these new synthetic methods, Dr. Watson and his students will seek to elucidate the underlying mechanism(s) of the transformations under study. Therefore, this project will provide exposure to synthetic, mechanistic and physical organic chemistry for the student and postdoctoral co-workers on the team, and in this way prepare them well for future careers in industry or academia.

This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.