Publication Date


Document Type


First Advisor

Gilbert, Thomas M.||Adler, Marc Jordan, 1981-

Degree Name

Ph.D. (Doctor of Philosophy)

Legacy Department

Department of Chemistry and Biochemistry


Organic chemistry; Chemistry


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.


Advisors: Thomas M. Gilbert; Marc J. Adler.||Committee members: Timothy Hagen; Douglas Klumpp; Carol Thompson.||Includes illustrations.||Includes bibliographical references.


179 pages




Northern Illinois University

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