Construction of Carbon–Fluorine Bonds Through Catalytic Nucleophilic Fluorination

Author: Wang, Zhuoyan

Year: 2027

Degree: Dissertation (Ph.D.)

Advisor: Fu, Gregory C.

Committee Members: Reisman, Sarah E.; Peters, Jonas C.; Stoltz, Brian M.; Fu, Gregory C.

Option: Chemistry

DOI: 10.7907/11xy-dx16

Abstract

The importance of organofluorine compounds in disciplines such as agriculture, materials science and medicine has stimulated a long-standing interest among chemists in developing novel synthetic methods to access fluorine-containing molecules. Despite the tremendous success in the construction of C(sp2)–F bonds, the synthesis of alkyl fluorides involving C(sp3)–F bond formation remains relatively underdeveloped and relies heavily on electrophilic fluorinating agents (e.g., NFSI and SelectFluor). Nucleophilic alternatives (e.g., CsF and KF), although more economical and atom-efficient, have rarely been applied in fluorination reactions, probably because of facile side-reactions such as elimination that affords olefin. Herein, this dissertation primarily discusses the progress towards developing novel nucleophilic fluorination strategies, focusing on method development with preliminary mechanistic investigations.

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