Author ORCID Identifier
Document Type
Thesis
Date of Award
2025
Degree Name
Master of Science (MS)
Department
Chemistry
First Advisor
Haoran HS Sun
Abstract
Converting a hydroxyl group into a better leaving group is a key step for nucleophilic substitution reactions involving alcohols and phenols, where direct hydroxyl displacement is ineffective. Approaches such as tosylation and triflation are well-established strategies in synthetic chemistry. Here, we present a simplified activation approach utilizing electron-deficient fluoroaromatic compounds. This method offers a practical and efficient alternative, enabling the conversion of alcohol into reactive derivatives under mild, operationally simple conditions. In parallel, the development of new reagents for nucleophilic fluorination is crucial for advancing synthetic methodologies in pharmaceutical and materials science. Traditional fluoride sources, such as anhydrous tetramethylammonium fluoride (TMAF) and anhydrous tetrabutylammonium fluoride (TBAF), are often hindered by moisture sensitivity and cation decomposition via the Hofmann elimination pathway. To overcome these challenges, we report the utilization of a bis-alkyl-amino-pyridine reagent that reacts with electron-deficient fluoroaromatic compounds and rapidly generates anhydrous fluoride salts in-situ.
Subject Categories
Chemistry | Organic Chemistry
Keywords
nucleophilic substitution reactions anhydrous tetrabutylammonium fluoride (TBAF)
Number of Pages
166
Publisher
University of South Dakota
Recommended Citation
Sharma, Amit, "Advancing Nucleophilic Fluorination: Synthesis of Alcohol Intermediates and Development of “Naked” Fluoride Source" (2025). Dissertations and Theses. 342.
https://red.library.usd.edu/diss-thesis/342