Cody Ross Pitts

The CRP Laboratory boasts a brand new, energetic, and enthusiastic organic chemistry research program at UC Davis. Research in this group will offer a diverse training experience in synthetic and physical organic chemistry at the nexus of method development, reagent design, total synthesis, and mechanistic studies, and takes inspiration from thinking about unusual retrosynthetic disconnections and "impossible" reactions. Potential future directions include topics pertaining to C-C bond activation, C-O bond formation, and the synthesis and evaluation of virtually unexplored (fluorinated) functional groups.

Education, Awards and Professional Highlights

• NIH Postdoctoral Fellow, Scripps Research Institute (2019-2021)
• ETH Postdoctoral Fellow, ETH Zurich (2017-2019)
• Ph.D. Johns Hopkins (2017)
• B.S. Monmouth University (2010)

Representative Publications

• 33. Peters, D. S.;† Pitts, C. R.;† McClymont, K. S.; Stratton, T. P.; Bi, C.; Baran, P. S.* "Ideality in Context: Motivations for Total Synthesis" Acc. Chem. Res. 2021, Accepted.
• 32. Liebing, P.;* Pitts, C. R.; Reimann, M.; Trapp, N.; Rombach, D.; Bornemann, D.; Kaupp, M.; Togni, A. "The Supramolecular Structural Chemistry of Pentafluorosulfanyl and Tetrafluorosulfanylene Compounds" Chem. Eur. J. 2021, Accepted.
• 31. Bornemann, D.; Brüning, F.; Bartalucci, N.; Wettstein, L.; Pitts, C. R.* "Examining Trichloroisocyanuric Acid and Oxalyl Chloride in Complementary Approaches to Fluorination of Group XV Heteroatoms" Helv. Chim. Acta 2021, Accepted.
• 30. Bornemann, D.; Pitts, C. R.; Wettstein, L.; Brüning, F.; Küng, S; Guan, L.; Trapp, N.; Grützmacher, H.;* Togni, A.* "Deoxygenative Fluorination of Phosphine Oxides: A General Route to Fluorinated Organophosphorus(V) Compounds and Beyond" Angew. Chem. Int. Ed. 2020, 59, 22790-22795.
• 29. Ghorbani, F.;† Harry, S. A.;† Capilato, J. N.; Pitts, C. R.; Joram, J.; Peters, G. N.; Tovar, J. D.; Smajlagic, I.; Siegler, M. A.; Dudding, T.;* Lectka, T.* "Carbonyl-Directed Aliphatic Fluorination: A Special Type of HAT Beats Out Norrish II" J. Am. Chem. Soc. 2020, 142, 14710-14724.
• 28. Capilato, J. N.; Pitts, C. R.; Rowshanpour, R.; Dudding, T.;* Lectka, T.* "Site-Selective Photochemical Fluorination of Ketals: Unanticipated Outcomes in Selectivity and Stability" J. Org. Chem. 2020, 85, 2855-2864.
• 27. Holl, M. G.; Pitts, C. R.; Lectka, T.* "Quest for a Symmetric [C-F-C]+ Fluoronium Ion in Solution: A Winding Path to Ultimate Success" Acc. Chem. Res. 2020, 53, 265-275.
• 26. Brüning, F.;† Pitts, C. R.;† Kalim, J.; Bornemann, D.; Ghiazza, C.; de Montmillon, J.; Trapp, N.; Billard, T.;* Togni, A.* "Difluoro(aryl)(perfluoroalkyl)-λ4-sulfanes and Selanes: Missing Links of Trichloroisocyanuric Acid/Potassium Fluoride Chemistry" Angew. Chem. Int. Ed. 2019, 58, 18937-18941.
• 25. Bornemann, D.;† Pitts, C. R.;†* Ziegler, C. J.; Pietrasiak, E.; Trapp, N.; Santschi, N.;* Togni, A.* "Pentafluoro(aryl)-λ6-tellanes and Tetrafluoro(aryl)(trifluoromethyl)-λ6-tellanes: From SF5 to the TeF5 and TeF4CF3 Groups” Angew. Chem. Int. Ed. 2019, 58, 12604-12608.
• 24. Liu, G.; Ciborowski, S. M.; Pitts, C. R.; Graham, J. D.; Buytendyk, A.; Lectka, T.; Bowen, K.* "Observation of the Dipole- and Quadrupole-Bound Anions of 1,4-Dicyanocyclohexane" Phys. Chem. Chem. Phys. 2019, 21, 18310-18315.
• 23. Häfliger, J.;† Pitts, C. R.;† Bornemann, D.; Käser, R.; Santschi, N.; Charpentier, J.; Otth, E.; Trapp, N.; Verel, R.; Lüthi, H. P.; Togni, A.* "Substituent-controlled, Mild Oxidative Fluorination of Iodoarenes: Synthesis and Structural Study of Aryl I(III)- and I(V)-Fluorides" Chem. Sci. 2019, 10, 7251-7259.
• 22. Young, J. D.; Honick, C. R.; Zhou, J.; Pitts, C. R.; Ghorbani, F.; Peters, G. M.; Lectka, T.; Tovar, J. D.; Bragg, A. E.* "Energy- and Conformer-Dependent Excited-State Relaxation of an E/Z Photoswitchable Thienyl-Ethene" Phys. Chem. Chem. Phys. 2019, 21, 14440-14452.
• 21. Pitts, C. R.;* Bornemann, D.; Liebing, P.; Santschi, N.;* Togni, A.* "Making the SF5 Group More Accessible: A Gas Reagent-free Approach to Aryl Tetrafluoro-λ6-sulfanyl Chlorides" Angew. Chem. Int. Ed. 2019, 58, 1950-1954.
• 20. Santschi, N.;* Pitts, C. R.; Jelier, B. J.; Verel, R. "Determining the predominant tautomeric structure of iodine-based group-transfer reagents by 17O NMR spectroscopy" Beilstein J. Org. Chem. 2018, 14, 2289–2294.
• 19. Bume, D. D.; Harry, S. A.; Lectka, T.;* Pitts, C. R.* "Catalyzed and Promoted Aliphatic Fluorination" J. Org. Chem. 2018, 83, 8803-8814.
• 18. Pitts, C. R.; Holl, M. G.; Lectka, T.* "Spectroscopic Characterization of a [C-F-C]+ Fluoronium Ion in Solution" Angew. Chem. Int. Ed. 2018, 57, 1924-1927.
• 17. Bume, D. D.; Harry, S. A.; Pitts, C. R.; Lectka, T.* "Sensitized Aliphatic Fluorination Directed by Terpenoidal Enones: A 'Visible Light' Approach" J. Org. Chem. 2018, 83, 1565-1575.
• 16. Holl, M. G.; Pitts, C. R.; Lectka, T.* "Fluorine in a C-F Bond as the Key to Cage Formation" Angew. Chem. Int. Ed. 2018, 57, 2758-2766.
• 15. Guan, L.; Holl, M. G.; Pitts, C. R.; Struble, M. D.; Siegler, M. A.; Lectka, T.* “Through-space Activation can Override Substituent Effects in Electrophilic Aromatic Substitution” J. Am. Chem. Soc. 2017, 139, 14913-14916.
• 14. Bume, D. D.;† Pitts, C. R.;† Ghorbani, F.; Harry, S. A.; Capilato, J. N.; Siegler, M. A.; Lectka, T.* “Ketones as Directing Groups in Photocatalytic sp3 C-H Fluorination” Chem. Sci. 2017, 8, 6918-6923.
• 13. Pitts, C. R.; Siegler, M. A.; Lectka, T.* "Intermolecular Aliphatic C-F•••H-C Interaction in the Presence of ‘Stronger’ Hydrogen Bond Acceptors: Crystallographic, Computational, and IR Studies" J. Org. Chem. 2017, 82, 3996-4000.
• 12. Pitts, C. R.; Bume, D. D.; Harry, S. A.; Siegler, M. A.; Lectka, T.* "Multiple Enone-Directed Reactivity Modes Lead to the Selective Photochemical Fluorination of Polycyclic Terpenoid Derivatives" J. Am. Chem. Soc. 2017, 139, 2208-2211.
• 11. Bume, D. B.; Pitts, C. R.; Jokhai, R. T.; Lectka, T.* "Direct, visible light-sensitized benzylic C-H fluorination of peptides using dibenzosuberenone: selectivity for phenylalanine-like residues" Tetrahedron 2016, 72, 6031-6036.
• 10. Pitts, C. R.; Ling, B.; Snyder, J. A.; Bragg, A. E.;* Lectka, T.* "Aminofluorination of Cyclopropanes: A Multifold Approach through a Common, Catalytically Generated Intermediate" J. Am. Chem. Soc. 2016, 138, 6598-6609.
• 9. Bume, D. D.; Pitts, C. R.; Lectka T.* "Tandem C-C Bond Cleavage of Cyclopropanols and Oxidative Aromatization by Manganese(IV) Oxide in a Direct C-H to C-C Functionalization of Heteroaromatics" Eur. J. Org. Chem. 2016, 2016, 26-30.
• 8. Pitts, C. R.; Bloom, M. S.; Bume, D. D.; Zhang, Q. A.; Lectka, T.* "Unstrained C-C Bond Activation and Directed Fluorination through Photocatalytically-Generated Radical Cations" Chem. Sci. 2015, 6, 5225-5229.
• 7. Bloom, S.; Bume, D. D.; Pitts, C. R.; Lectka, T.* "Site-Selective Approach to β-Fluorination: Photocatalyzed Ring Opening of Cyclopropanols" Chem. Eur. J. 2015, 21, 8060-8063.
• 6. Pitts, C. R.; Ling, B.; Woltornist, R.; Liu, R.; Lectka, T.* "Triethylborane-Initiated Radical Chain Fluorination: A Synthetic Method Derived from Mechanistic Insight" J. Org. Chem. 2014, 79, 8895-8899.
• 5. Pitts, C. R.; Bloom, S.; Woltornist, R.; Auvenshine, D.; Ryzhkov, L. R.; Siegler, M. A.; Lectka, T.* "Direct, Catalytic Monofluorination of sp3 C‑H Bonds: A Radical-Based Mechanism with Ionic Selectivity" J. Am. Chem. Soc. 2014, 136, 9780-9791.
• 4. Pitts, C. R.; Lectka, T.* "Chemical Synthesis of β-Lactams: Asymmetric Catalysis and Other Recent Advances" Chem. Rev. 2014, 114, 7930-7953.
• 3. Bloom, S.; Pitts, C. R.; Woltornist, R.; Griswold, A.; Holl, M. G.; Lectka, T.* "Iron(II)-Catalyzed Benzylic Fluorination" Org. Lett. 2013, 15, 1722-1724.
• 2. Bloom, S.; Pitts, C. R.; Miller, D. C.; Haselton, N.; Holl, M. G.; Urheim, E.; Lectka, T.* "A Polycomponent Metal-Catalyzed Aliphatic, Allylic, and Benzylic Fluorination" Angew. Chem. Int. Ed. 2012, 51, 10580-10583.
• 1. Anderson, S.;* Pitts, C. R. "Art, science and the staying power of the beat in Bring in 'Da Noise, Bring in 'Da Funk" Studies in Musical Theatre 2012, 6, 227-236.