New Silicon-Based Strategies for Organic Synthesis

Northwestern University, Evanston IL

Investigators

Abstract

The principal goal of this research program is the discovery of new, unconventional reagents and their development as tools for chemical synthesis. This plan outlines a comprehensive approach to the development of new catalytic reactions using organosilicon compounds. Acylsilanes are silicon-containing small molecules that have been investigated for over 30 years due to their unusual reactivity (e.g., acyl anions), yet there remains many opportunities to exploit and utilize these unique compounds in chemical synthesis. Silyloxyallenes are versatile compounds with significant potential in cycloadditions, tandem bond-forming sequences and group transfer reactions. By integrating the reactivity of these unique enolsilanes with tandem or subsequent reactions, the PI will be able to access important compound classes with high efficiency and minimal waste. The complementary mechanistic and target-oriented approaches driving this work allows for studies that are unique among current investigations in organosilicon and catalysis research. The group is developing sophisticated and highly versatile methods for the convergent construction of new small molecules that have broad utility. Broader Impact: The investigation of the research goals of this proposal will simultaneously provide the undergraduate students, graduate students, postdoctoral fellows and visiting scholars working on these projects with essential experience and scientific knowledge. They will learn synthesis techniques, instrumentation analysis, organometallic chemistry, purification science, and problem solving strategies. In addition to acquiring laboratory skills, the Scheidt team has regular weekly full group meetings and daily sub-group gatherings to discuss prior results and chart new research directions. Weekly meetings include research presentations, short discussions on recent high-impact publications, and chemical problems for pedagogical growth. Overall, the individual training in the laboratory combined with small, medium and large group formats for presenting and discussing chemical topics provides for a rich, vibrant and dynamic learning environment. Additionally, there is strong participation by underrepresented groups in the laboratory which engenders a professional, dynamic and multi-ethnic work environment. Professor Scheidt will continue to organize and host the annual Chicago Organic Symposium as well as strengthen ties with institutions such as Western Michigan University and Chicago State University. This outreach component is centered on creating an interchange of ideas throughout the Department of Chemistry and between academic and industrial personnel from a variety of backgrounds and is expected to have a unique and significant impact on society.