Synthesis of Anti-Trisubstituted Vinylsilanes via Palladium Catalysis

• Andrew Richards, Chemistry, University of Delaware

• Donald Watson, Chemistry and Biochemistry, University of Delaware

Organosilanes, such as vinylsilanes, are non-toxic, useful reagents in cross-coupling reactions like the Hiyama reaction. In the Hiyama reaction, organosilanes can be activated externally or in situ to allow for a nucleophilic silicon molecule, which can undergo transmetallation followed by reductive elimination to form new carbon–carbon bonds. Methods for synthesizing syn-substituted terminal and internal vinylsilanes have been established in the literature, but systems to develop anti-substituted vinylsilanes are still underexplored. Herein, I will describe my efforts this summer to synthesize an anti-substituted vinylsilane via a series of optimization studies involving variables such as catalyst system, solvent, time, and temperature. This work is an extension of the work I completed during the Spring 2023 semester.