Nicholas D. Ball

Assistant Professor of Chemistry

nicholas.ball@pomona.edu

Office:

Seaver North

206

(909) 607-0378

Personal Website

With Pomona since:

2015

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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

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

B.A., Macalester College

Ph.D., University of Michigan

Post-doc, California Institute of Technology

Awards & Honors

NIGMS NIH R15 AREA grant (R15GM134457) 2020-2023.
Wig Distinguished Professor Award 2018
American Chemical Society; Petroleum Research Fund Grant UNI – 2014-2016
National Institutes of Health; Ruth L. Kirschstein Postdoctoral Fellow – 2011-2013
National Institutes of Health; Ruth L. Kirschstein Predoctoral Fellow – 2009-2011