Cody Ross Pitts

About

Cody Ross Pitts is an Assistant Professor in the Department of Chemistry at UC Davis. His research group, the CRP Laboratory, focuses on organic chemistry with an emphasis on synthetic and physical organic chemistry, method development, reagent design, total synthesis, and mechanistic studies. His work is inspired by unusual retrosynthetic disconnections and 'impossible' reactions, with potential future directions including C-C bond activation, C-O bond formation, and the synthesis and evaluation of unexplored fluorinated functional groups. Dr. Pitts has a distinguished educational background, earning his Ph.D. from Johns Hopkins University in 2017, followed by postdoctoral fellowships at ETH Zurich and the Scripps Research Institute. His research contributions include advancing fluorination techniques, exploring supramolecular chemistry, and developing new reagents and methods in organic synthesis. His publications reflect a strong focus on fluorine chemistry, organophosphorus compounds, and innovative approaches to chemical synthesis.

Research topics

• Chemistry
• Organic chemistry
• Stereochemistry
• Computer Science
• Computational chemistry
• Sociology
• Social Science
• Photochemistry
• Combinatorial chemistry
• Engineering

Selected publications

• Strain‐Release Pentafluorosulfanylation and Tetrafluoro(aryl)sulfanylation of [1.1.1]Propellane: Reactivity and Structural Insight**

  Angewandte Chemie International Edition · 2022 · 75 citations

  Senior authorCorresponding

  Ar radicals across [1.1.1]propellane, we accessed structurally unique bicyclopentanes, bearing two distinct elements of bioisosterism. Upon evaluating these "hybrid isostere" motifs in the solid state, we measured exceptionally short transannular distances; in one case, the distance rivals the shortest nonbonding C⋅⋅⋅C contact reported to date. This prompted SC-XRD and DFT analyses that support the notion that a donor-acceptor interaction involving the "wing" C-C bonds is playing an important ro…

  PublisherOA PDFDOI

• Overcoming a Radical Polarity Mismatch in Strain‐Release Pentafluorosulfanylation of [1.1.0]Bicyclobutanes: An Entryway to Sulfone‐ and Carbonyl‐Containing SF₅‐Cyclobutanes

  Angewandte Chemie International Edition · 2024-01-18 · 52 citations

  articleOpen accessSenior authorCorresponding

  Abstract The first assortment of achiral pentafluorosulfanylated cyclobutanes (SF 5 ‐CBs) are now synthetically accessible through strain‐release functionalization of [1.1.0]bicyclobutanes (BCBs) using SF 5 Cl. Methods for both chloropentafluorosulfanylation and hydropentafluorosulfanylation of sulfone‐based BCBs are detailed herein, as well as proof‐of‐concept that the logic extends to tetrafluoro(aryl)sulfanylation, tetrafluoro(trifluoromethyl)sulfanylation, and three‐component pentafluorosulf…

  PublisherOA PDFDOI

• Direct <i>N</i> –SF ₅ and <i>N</i> –SF ₄ CF ₃ Bond Formation through Strain-Release Functionalization of 3-Substituted [1.1.0]Azabicyclobutanes

  Journal of the American Chemical Society · 2025-07-23 · 24 citations

  articleSenior authorCorresponding

  In comparison to modern methods for carbon–SF5 bond formation, methods for direct heteroatom–SF5 bond formation are exceptionally scarce, rendering motifs such as “N–SF5” virtually unexplored in the context of organic and medicinal chemistry. Herein, we demonstrate that direct N–SF5 bond formation can be accomplished through strain-release pentafluorosulfanylation of 3-aryl [1.1.0]azabicyclobutanes (ABBs), using an easy-to-access solution of SF5Cl. To our surprise, the resultant N–SF5 azetidines…

  PublisherDOI

• Strain-release trifluoromethoxylation and pentafluorosulfanoxylation of [1.1.0]bicyclobutanes: expanded access to fluorinated cyclobutane hybrid bioisosteres

  Chemical Communications · 2024-12-19 · 17 citations

  articleOpen accessSenior authorCorresponding

  Methods for formal bromo-trifluoromethoxylation and bromo-pentafluorosulfanoxylation of [1.1.0]bicyclobutanes using AgOCF 3 or AgOSF 5 and 1,3-dibromo-5,5-dimethylhydantoin are disclosed.

  PublisherOA PDFDOI

• Competition between C–C and C–H Bond Fluorination: A Continuum of Electron Transfer and Hydrogen Atom Transfer Mechanisms

  Journal of the American Chemical Society · 2023-10-04 · 15 citations

  articleSenior authorCorresponding

  In 2015, we reported a photochemical method for directed C–C bond cleavage/radical fluorination of relatively unstrained cyclic acetals using Selectfluor and catalytic 9-fluorenone. Herein, we provide a detailed mechanistic study of this reaction, during which it was discovered that the key electron transfer step proceeds through substrate oxidation from a Selectfluor-derived N-centered radical intermediate (rather than through initially suspected photoinduced electron transfer). This finding le…

  PublisherDOI

Recent grants

• Synthetic Methods to Make Emerging Fluorinated Groups More Accessible

  NIH · $1.1M · 2023–2028

Frequent coauthors

• Thomas Lectka

  Johns Hopkins University

  64 shared

• Antonio Togni

  42 shared

• Dustin Bornemann

  41 shared

• Nils Trapp

  ETH Zurich

  32 shared

• Desta Doro Bume

  Frederick National Laboratory for Cancer Research

  23 shared

• Yannick Kraemer

  22 shared

• Nico Santschi

  University of Münster

  22 shared

• Clément Ghiazza

  21 shared

Labs

• CRP LaboratoryPI

Education

• Ph.D. in Organic Chemistry, Chemistry

  Johns Hopkins University

  2017

• B.S. in Chemistry with minors in Physics and Musical Theatre, Chemistry

  Monmouth University

  2010

Awards & honors

• Francesca Miller Undergraduate Research Award
• R.B. Miller Research, Service, and Mentorship Award
• R. Bryan Miller Summer Graduate Fellowship

Similar researchers at University of California, Davis

• Lee-Ping Wangh-41
• Chenchen Songh-29
• Elizabeth Neumannh-24