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.
Message to Sponsor
- Major: Chemistry
- Sponsor: Rose Hills Independent
- Mentor: John Hartwig