Undergraduate Research & Scholarships

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.

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.