PyFluor

The prevalence of organofluorine compounds in industry and drug design necessitates the ability to introduce C–F bonds to molecules.

Research in the Doyle group focuses on two areas: nucleophilic fluorination and nickel catalysis. The Doyle group has developed several reagents that advance these research areas. In fluorination, 2-pyridinesulfonyl fluoride (PyFluor) can be used for the mild deoxyfluorination of primary and secondary alcohols, a procedure which is normally accomplished by the sensitive reagent DAST. In nickel catalysis, the Doyle group has developed a modular, air-stable nickel precatalyst, [(TMEDA)Ni(o-tolyl)Cl], which has broad utility for a wide variety of reactions. This precatalyst can be used in place of Ni(cod)2, NiCl2, as well as other reported precatalysts. Doyle has also reported electron-deficient olefin ligands as a new class of ligand for accelerated reductive elimination. In particular, the sultam-derived ligand Fro-DO has been found to be critical for high yields in the cross-coupling of tertiary aziridines to form quaternary centers.