Date of Award
5-2026
Document Type
Dissertation
Degree Name
Doctor of Philosophy (PhD)
Department
Chemistry
Committee Chair/Advisor
Byoungmoo Kim
Committee Member
Dan Whitehead
Committee Member
Dev Arya
Committee Member
Rhett Smith
Abstract
The selective functionalization of abundant oxygen-containing functional groups into valuable products represents a central challenge in modern synthetic chemistry. This dissertation describes the development of deoxygenative platforms that selectively functionalize carboxylic acids and alcohols into structurally complex, nitrogen-containing compounds relevant to medicinal chemistry, drug discovery, and advance materials. A new TiIV multicatalytic platform was developed to catalytically modify each C–O bond of carboxylic acid to C–C, C–N, and C–H bonds to furnish enantio-enriched a-amino nitriles up to 98:2 er. Towards the diversification of alcohols, a sulfur (VI) fluoride exchange (SuFEx)-enabled platform was established to facilitate the direct conversion of C–O bonds in complex hydroxy-containing molecules into C(sp³)–N bonds, affording a broad range of complex alkylamines in high yields with excellent stereospecificity (>20:1 dr) and no elimination side-products.
Recommended Citation
Gutierrez, Giovani, "Deoxy-Diversification of Carboxylic Acids and Alcohols" (2026). All Dissertations. 4265.
https://open.clemson.edu/all_dissertations/4265