Gilbert, Thomas M.||Adler, Marc Jordan, 1981-
Ph.D. (Doctor of Philosophy)
Department of Chemistry and Biochemistry
In this work 1-Hydrosilatrane has shown great potential to be a commodity reducing reagent in organic synthesis. Initially, 1-hydrosilatrane was investigated as a reducing reagent in the transformation of aldehydes to corresponding alcohols. Although initial investigations did not confirm previously published work, after addition of a Lewis base activator 1-hydrosilatrane demonstrated speedy reductions of many functionalized aryl aldehydes to alcohols with good yields. Next, 1- hydrosilatrane was used in a direct reductive amination reaction between primary amines and aldehydes/ketones. Reaction proceeded in the presence of a Bronsted acid, and resulted in excellent yields. This reaction was then expanded to chiral Bronsted acids and demonstrated the potential of 1-hydrosilatrane as a reagent in chiral reactions with enantiomeric excess of up to 84%. This work demonstrates versatility of 1-hydrosilatrane and presents it as a must have reagent in every organic chemistry lab.
Skrypai, Vladislav, "Application of 1-hydrosilatrane as a robust reducing reagent" (2018). Graduate Research Theses & Dissertations. 1496.
Northern Illinois University
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