SURF

Jonathan Yang

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

The SURF Rose Hills fellowship allowed me to continue my research into the summer, and I am very appreciative of that. Over the summer there was significant progress in my project, a copper catalyzed SN2' to form borylated (Z)-fluoroalkenes with application to medical chemistry. The reaction was improved to give nearly perfect yield and selectivity, shown to work over a broad range of electrophile substrates, and the synthetic utility was also demonstrated. I plan on finishing the project soon, and hope to publish. This work, along with other chemistry experiences, has inspired me to take the next step, and I hope to continue chemistry research in graduate school.
  • Major: Chemistry
  • Sponsor: Rose Hills Independent
  • Mentor: John Hartwig