Examining reactivity between boron Lewis acids and halogenated species

Within chemistry, boron Lewis acids are widely known for making strong bonds with fluorine. This ability can be useful when applied to C F activation, a field of chemistry that focuses on breaking one or more C F bonds from fluorine-containing molecules. Development in this field of research is of particular interest for its potential application in degrading persistent fluorinated waste that has no naturally occurring disposal. Additionally, C F activation can act as a compelling tool for the structural design and development of pharmaceuticals and agrochemicals.

The body of this thesis initially focuses on the literature methods that use trifluoromethyl arenes (ArCF₃) and boron Lewis acids to synthesize valuable difluoromethyl (ArCF₂R) and trihalomethyl (ArCX₃) arenes. Previous work performed by the Williams Lab highlighted an opportunity to expand upon the metal-catalyzed C F activation of ArCF₃ using boron trihalides (BX₃, X = Cl, Br). Fascinatingly, boron triiodide demonstrates rather peculiar behavior that diverges from the expectations established by the other BX₃ reagents. Over the course of this research, efforts were focused on the optimization of benzyl iodides (ArCH₂I) and 1-phenyladamantane products.

In addition, the development of a one-pot, gram-scale synthesis and purification of BI₃ for practical laboratory production led to the isolation of highly pure, crystalline BI₃ that was generated from readily available, affordable, and benchtop stable reagents. Altogether, the development of new C F activation strategies and the optimized large-scale synthesis of BI₃ underscores the versatility of boron reagents in fluorine chemistry.