Author ORCID Identifier
Semester
Spring
Date of Graduation
2024
Document Type
Thesis
Degree Type
MS
College
Eberly College of Arts and Sciences
Department
Chemistry
Committee Chair
Margaret Hilton
Committee Member
Brian Popp
Committee Member
Gregory Dudley
Abstract
Organofluorines are an omnipresent class of organic molecules, especially in pharmaceuticals. Selective fluorination of drug molecules allows for the influence of properties including metabolic activity, solubility, and intrinsic potency. Deoxyfluorinations are typically performed via generation of nucleophilic fluoride from a deoxyfluorination agent. Traditionally, diethylaminosulfur trifluoride (DAST) is the reagent of choice for these reactions, and it remains a popular reagent today. However, it has a propensity to form elimination side products and explode. Several research groups have recently developed new classes of deoxyfluorination agents including imidazole-based reagents (PhenoFluor) and sulfonyl fluorides (PyFluor) that exhibit better functional group tolerance and much safer handling. Brittain and Cobb have demonstrated pentafluoropyridine’s (PFP) utility in the synthesis of acyl fluorides from carboxylic acids. Based upon this research, we explore PFP and other fluoropyridines’ abilities to deoxyfluorinate alkyl alcohols.
Recommended Citation
Bias, Christopher Allen, "Investigation of Deoxyfluorination of Alkyl Alcohols Using Pentafluoropyridines through a Covalent Intermediate" (2024). Graduate Theses, Dissertations, and Problem Reports. 12392.
https://researchrepository.wvu.edu/etd/12392