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The introduction of fluoroalkyl groups into organic molecules is well-known to alter various chemical and physical properties that are important to the life sciences and materials fields. Evidence is observed in the pharmaceutical field where over 40% of new small molecule drugs in 2018 and 2019 contained fluorine. Likewise, over 50% of new agrochemicals since 1998 contained fluoroalkyl functionalities. Therefore, the development of synthetic strategies for introducing fluoroalkyl groups is imperative in organic synthesis. In this dissertation, new advances towards enabling fluoroalkylation with earth-abundant first-row transition metals copper, cobalt, and nickel, are described. With copper, a methodology for rapidly accessing and analyzing mixed fluoroalkyl cuprates is described. A family of fluoroalkyl cobalt(III) complexes have been prepared, and their solution and oxidative properties have been studied. Finally, a new strategy for fluoroalkylation is reported using simple nickel salts supported by solvato ligands.
Full Title
Advancing Fluoroalkylation Methodologies with Copper, Nickel, and Cobalt
Member of
Contributor(s)
Creator: Shreiber, Scott
Thesis advisor: Vicic, David
Date Issued
2022
Language
English
Type
Genre
Department name
Chemistry
Media type
Subject (LCSH)
Citation
@mastersthesis{shreiber2022,
title = {Advancing Fluoroalkylation Methodologies with Copper, Nickel, and Cobalt},
author = {Shreiber, Scott},
year = {2022},
keywords = {Cobalt, Copper, fluoroalkylation, Nickel, Organometallic, trifluoromethylation},
abstract = {The introduction of fluoroalkyl groups into organic molecules is well-known to alter various chemical and physical properties that are important to the life sciences and materials fields. Evidence is observed in the pharmaceutical field where over 40\% of new small molecule drugs in 2018 and 2019 contained fluorine. Likewise, over 50\% of new agrochemicals since 1998 contained fluoroalkyl functionalities. Therefore, the development of synthetic strategies for introducing fluoroalkyl groups is imperative in organic synthesis. In this dissertation, new advances towards enabling fluoroalkylation with earth-abundant first-row transition metals copper, cobalt, and nickel, are described. With copper, a methodology for rapidly accessing and analyzing mixed fluoroalkyl cuprates is described. A family of fluoroalkyl cobalt(III) complexes have been prepared, and their solution and oxidative properties have been studied. Finally, a new strategy for fluoroalkylation is reported using simple nickel salts supported by solvato ligands.},
language = {English},
}
