Research - Transformations with Sulfur and Fluorine
The Ball Laboratory is interested in developing new metal-catalyzed/-mediated organic reactions. Our focus is to develop methodologies to make and activate sulfur(VI) fluorides. In particular we are interested in using sulfur (VI) fluorides as a more air and water stable alternative to traditional synthesis of sulfur-based organic molecules. Our strategy is to achieve this goal by metal-catalyzed activation of sulfur(VI) fluorides via sulfur-fluorine exchange (SuFEx) to make sulfonylated compounds. Additionally, we have interest in sulfur (VI) fluorides in cross-coupling chemistry.
Our research involves a two-step strategy: 1) development of new catalytic reactions, and 2) mechanistic investigations of these reactions with model organometallic complexes. Experiments and results from each component facilitate the innovation in the other providing an impactful, deeper understanding of the chemistry. The goals of this research for students is to learn how to turn theory into practice, to critically work through scientific challenges, and to understand and take ownership of their work. Most importantly, I want students to appreciate and develop a love for science!
Students will gain extensive experience in organic and inorganic synthesis, metal catalysis, NMR spectroscopy, and physical organic chemistry. Students with a wide variety of interests are welcomed into our lab! Please explore the links below to learn more about the Ball Lab.
Publications
Independent Career (underline denotes undergraduate co-authors)
Google scholar citations
Research Gate
Independent Career (underline denotes undergraduate co-authors)
Google scholar citations
Research Gate
- Rueda-Espinosa, J.; Ramanayake, D.; Ball, N. D.; Love, J. A. Synthesis of 2-arylpyridines by the Suzuki-Miyaura cross- coupling of PyFluor with hetero(aryl) boronic acids and esters. Can. J. Chem. 2023, Just accepted.
- Carneiro, S. N.; Khasnavis, S. R.; Lee, J.; Butler, T. W.; Majmudar, J. D.; am Ende, C. W.; and Ball, N.D. Sulfur(VI) Fluorides as Tools in Biomolecular and Medicinal Chemistry. Org. Biomol. Chem. 2023, 8, 907-909. [link][PDF]
- Thomson B. J.; Khasnavis, S. R.; Grigorian, E. C.; Krishnan, R.; Yassa, T. D.; Lee, K. L.; Sammis, G. M.; and Ball, N. D. Facile synthesis of sulfonyl fluorides from sulfonic acids. Chem. Commun. 2023, 59, 555-558. [link][PDF] (Cover)
4. Han, B.; Khasnavis, S. R.; Nwerem, M; Bertagna, M; Ball, N. D., and Ogba, O. M. Calcium Bistriflimide-Mediated Sulfur(VI)–Fluoride
Exchange (SuFEx): Mechanistic Insights toward Instigating Catalysis. Inorg. Chem. 2022, 61, 9746-9755. [link]
5. Ball, Sulfondiimidamides unlocked as new S(VI) hubs for synthesis and drug discovery, Chem (2022), https://
doi.org/10.1016/j.chempr.2022.03.018 [link] [Pubmed free]
6. Carneiro, S.N.; Ball, N.D.; Lee, J.; and am Ende, C.W. (2021). [4-(Acetylamino)phenyl]imidodisulfuryl Difluoride. In Encyclopedia of
Reagents for Organic Synthesis. https://doi.org/10.1002/047084289X.rn02400 [link]
7. Lee, C.; Cook, L; Elisabeth, J. E.; Friede, N. C.; Sammis, G. M.; Ball, N.D. The Emerging Applications of Sulfur (VI) Fluorides in Catalysis.
ACS Catalysis. 2021, 11, 6578-6589. [link][PDF]
8. Mahapatra, S.; Woroch, C. P. ; Butler, T. W.; Carneiro, S. N. ; Kwan, S. C. ; Khasnavis, S. R. ; Gu, J.; Dutra, J. K. ; Vetelino, B. C.;
Bellenger, J.; am Ende, C. W.; and Ball, N. D. SuFEx Activation with Ca(NTf2)2: A Unified Strategy to Access Sulfamides, Sulfamates
and Sulfonamides from S(VI) Fluorides. Org. Lett. 2020, 22, 4389–4394. [Iink][PDF]
9. Ball, N. D. "Properties and Applications of S(VI) Fluorides" in Emerging Fluorinated Motifs. Properties, Synthesis and Applications,
Cahard, D., Ma, J.–A., Eds.; Wiley-VCH Verlag GmbH & Co: Weinheim, 2020: 621-674.
10. Lee, C.; Ball, N. D.; Sammis, G. M One-Pot Fluorosulfurylation of Grignard Reagents Using Sulfuryl Fluoride. Chem. Comm. 2019, 55,
14753-14756. [link]
11. Mukherjee, P.; Woroch, C. P..; Cleary, L.; Rusznak, M.; Franzese, R. W.; Reese, M. R.; Tucker, J. W.; Humphrey, J. M.; Etuk, S. M.;
Kwan, S. C.; am Ende, C. W.; and Ball, N. D. Sulfonamide Synthesis via Calcium Triflimide Activation of Sulfonyl Fluorides. Org. Lett.
2018, 20, 3943-3947. [link][PDF]
12. Tribby, A. L.; Rodríguez, I.; Shariffudin, S.; Ball, N. D. Pd-Catalyzed Conversion of Aryl Iodides to Sulfonyl Fluorides Using SO2
Surrogate DABSO and Selectfluor. J. Org. Chem. 2017, 82, 2294-2299. [link][PDF]
– This work is featured in a virtual issue of Organometallics called, "Undergraduate Research: Contributions
to Organometallic Chemistry". [link]
Graduate work:
Exchange (SuFEx): Mechanistic Insights toward Instigating Catalysis. Inorg. Chem. 2022, 61, 9746-9755. [link]
5. Ball, Sulfondiimidamides unlocked as new S(VI) hubs for synthesis and drug discovery, Chem (2022), https://
doi.org/10.1016/j.chempr.2022.03.018 [link] [Pubmed free]
6. Carneiro, S.N.; Ball, N.D.; Lee, J.; and am Ende, C.W. (2021). [4-(Acetylamino)phenyl]imidodisulfuryl Difluoride. In Encyclopedia of
Reagents for Organic Synthesis. https://doi.org/10.1002/047084289X.rn02400 [link]
7. Lee, C.; Cook, L; Elisabeth, J. E.; Friede, N. C.; Sammis, G. M.; Ball, N.D. The Emerging Applications of Sulfur (VI) Fluorides in Catalysis.
ACS Catalysis. 2021, 11, 6578-6589. [link][PDF]
8. Mahapatra, S.; Woroch, C. P. ; Butler, T. W.; Carneiro, S. N. ; Kwan, S. C. ; Khasnavis, S. R. ; Gu, J.; Dutra, J. K. ; Vetelino, B. C.;
Bellenger, J.; am Ende, C. W.; and Ball, N. D. SuFEx Activation with Ca(NTf2)2: A Unified Strategy to Access Sulfamides, Sulfamates
and Sulfonamides from S(VI) Fluorides. Org. Lett. 2020, 22, 4389–4394. [Iink][PDF]
9. Ball, N. D. "Properties and Applications of S(VI) Fluorides" in Emerging Fluorinated Motifs. Properties, Synthesis and Applications,
Cahard, D., Ma, J.–A., Eds.; Wiley-VCH Verlag GmbH & Co: Weinheim, 2020: 621-674.
10. Lee, C.; Ball, N. D.; Sammis, G. M One-Pot Fluorosulfurylation of Grignard Reagents Using Sulfuryl Fluoride. Chem. Comm. 2019, 55,
14753-14756. [link]
11. Mukherjee, P.; Woroch, C. P..; Cleary, L.; Rusznak, M.; Franzese, R. W.; Reese, M. R.; Tucker, J. W.; Humphrey, J. M.; Etuk, S. M.;
Kwan, S. C.; am Ende, C. W.; and Ball, N. D. Sulfonamide Synthesis via Calcium Triflimide Activation of Sulfonyl Fluorides. Org. Lett.
2018, 20, 3943-3947. [link][PDF]
12. Tribby, A. L.; Rodríguez, I.; Shariffudin, S.; Ball, N. D. Pd-Catalyzed Conversion of Aryl Iodides to Sulfonyl Fluorides Using SO2
Surrogate DABSO and Selectfluor. J. Org. Chem. 2017, 82, 2294-2299. [link][PDF]
– This work is featured in a virtual issue of Organometallics called, "Undergraduate Research: Contributions
to Organometallic Chemistry". [link]
Graduate work:
- Racowski, J. M.; Ball, N. D.; Sanford, M. S. Aryl C–H Activation at Pd(IV) Centers. J. Am. Chem. Soc. 2011, 133, 18022-18025. [link]
- Ball, N. D.; Gary, J. B.; Ye, Y.; Sanford, M. S. Mechanistic and Computational Studies of Oxidatively-Induced Aryl–CF3 Bond-Formation at Pd: Rational Design of Room Temperature Aryl Trifluoromethylation. J. Am. Chem. Soc. 2011, 133, 7577-7584. [link]
- Ye, Y.; Ball, N. D.; Kampf, J. W.; Sanford, M. S. Oxidation of Catalytically Relevant Palladium Dimer with “CF3+: Formation and Reactivity of a Monomeric Palladium(IV) Aquo Complex. J. Am. Chem. Soc. 2010, 132, 14682-14687. [link]
- Ball, N. D.; Kampf, J. W.; Sanford, M. S. Aryl C–CF3 Bond Forming Reductive Elimination from a Palladium(IV) Complex. J. Am. Chem. Soc. 2010, 132, 2878-2879. [link]
- Ball, N. D.; Kampf, J. W.; Sanford, M. S. Synthesis and Reactivity of Palladium(II) Fluoride Complexes Containing Nitrogen-Donor Ligands. Dalton Trans. 2010, 39, 632-640. [link]
- Ball, N. D.; Sanford, M. S. Synthesis and Reactivity of a Mono-sigma-Aryl Palladium(IV) Fluoride Complex. J. Am. Chem. Soc. 2009, 131, 3796-3797. [link]
