Cody Ross Pitts- UC Davis
https://www.codyrosspittslab.com/
Strain-Release Pentafluorosulfanylation: Strange Molecules Doing Stranger Things
Abstract: This presentation details recent progress in our laboratory toward the synthesis and evaluation of historically underemployed fluorinated functional groups that have been made more accessible using the TCICA/KF approach to oxidative fluorination. A major theme will be our recent merging of SF5 radical chemistry with strain-release functionalization of [1.1.1]propellane, [1.1.0]bicyclobutanes, and [1.1.0]azabicyclobutanes. Structural consequences of making these SF5-based "hybrid bioisosteres" and preliminary mechanistic insight will be discussed. Aside from being a topic of fundamental interest, we believe this work affords an unusual and subtle type of flexibility in molecular design that could prove useful in increasing availability of building blocks containing C(sp3)–SF5 and heteroatom–SF5 bonds to medicinal chemists, agrochemists, and in the materials community.
Bio: Cody Ross Pitts received a B.S. in Chemistry with minors in Physics and Musical Theatre from Monmouth University in 2010. In 2017, he received his Ph.D. in Chemistry from Johns Hopkins University with Prof. Thomas Lectka; his research was centered on synthetic and physical organic chemistry, including development of radical fluorination chemistry and the first spectroscopic observation of a stable fluoronium ion in solution. From 2017–2019, Cody conducted research on inorganic fluorine chemistry with Prof. Antonio Togni at ETH Zürich under an ETH Postdoctoral Fellowship. From 2019–2021, Cody conducted research in total in synthesis with Prof. Phil S. Baran at The Scripps Research Institute under an NIH Postdoctoral Fellowship. In July 2021, Cody began his independent career at UC Davis and has established a research program that provides training in reagent design, method development, mechanistic studies, and organic synthesis.