Nicholas D. Ball

Associate Professor of Chemistry; On leave for the 2024-2025 academic year
nicholas.ball@pomona.edu
Office:
Seaver North
206

(909) 607-0378

With Pomona Since: 2015
Nicholas Ball
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  • Expertise

    Expertise

    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.

    Areas of Expertise

    • Organometallic Chemistry
    • Organic Chemistry
    • Homogeneous Catalysis
    • Physical Organometallic Chemistry
  • Work

    Work

    Chappell, W.P.; Schur, N.; Vogel, J. A.; Sammis, G. M.; Melvin, P. E.; Ball, N.D. Poison to promise: The resurgence of organophosphorus fluoride chemistry. Chem. 2024, P1644-1654.

    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, 101, 765-772.

    Carneiro, S. N.; Khasnavis, S. R. (PO ; 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.

    Thomson B. J.; Khasnavis, S. R.; Grigorian, E. C.; Krishnan, R.; Yassa, T. D.; Lee, K. L.; Sammis, G. M.; and Ball, N. D., Chem. Commun. 2023, Chem. Commun. 2023, 59, 555-558. 

    Brian Han, Samuel R. Khasnavis, Matthew Nwerem, Michael Bertagna, Nicholas D. Ball, O. Maduka Ogba. Calcium Bistriflimide-Mediated Sulfur(VI)–Fluoride Exchange (SuFEx): Mechanistic Insights toward Instigating Catalysis. Inorg. Chem.2022, 61, 9746-9755.

    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

    Carneiro, S.N., Ball, N.D., Lee, J. and Ende, C.W. (2021). [4-(Acetylamino)phenyl]imidodisulfuryl Difluoride. In Encyclopedia of Reagents for Organic Synthesis.

    Lee, C.; Cook, L; Elisabeth, J. E. (’22); Friede, N. C. (’22).; Sammis, G. M.; Ball, N.D. The Emerging Applications of Sulfur (VI) Fluorides in Catalysis. ACS Catalysis. 2021, 11, 6578-6589.

    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.

    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.

    Lee, C.; Ball, N.B.*; Sammis, G. M* One-Pot Fluorosulfurylation of Grignard Reagents Using Sulfuryl Fluoride. Chem. Comm. 2019, 55, 14753-14756.

    Mukherjee, P.; Woroch, C. P. W.*; 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.

    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. DOI: 10.1021.

    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.

    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.

    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.

    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.

    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.

    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.

  • Education

    Education

    B.A., Macalester College

    Ph.D., University of Michigan

    Post-doc, California Institute of Technology

  • Awards & Honors

    Awards & Honors

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Claremont, CA 91711

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