Jonathan Yang Rose Hills
Copper Catalyzed SN2 Functionalization of Fluoroalkylated Alkenes
The introduction of fluorinated moieties into pharmaceuticals can often predictably improve the lipophilicity, metabolic stability, and the conformation of drugs. A fluorinated functional group of interest is the (Z)-fluoroalkene, a non-hydrolyzable isostere for peptide bonds. Many methods used to prepare fluoroalkenes, including Wittig-type olefinations, Shapiro reactions, and bromofluorination/elimination reactions often provide olefins in low stereoselectivity. Herein we will present a copper-catalyzed SN2 substitution of fluoroalkylated alkenes to prepare a variety of (Z)-fluoroalkenes in excellent stereoselectivities.