Thomas, Andy A. - Texas A&M University - Department of Chemistry

个人简介

Andy Thomas was born in Oakboro, NC in 1988. He received both his B.S. and M.S. degrees in chemistry from the University of North Carolina at Charlotte with Prof. Craig A. Ogle. At UNCC he investigated the mechanisms of various organocuprate reactions, such as the conjugate addition, alkylation and allylation reactions. In 2011 he moved to the university of Illinois at Urbana Champaign to begin his Ph.D. with Prof. Scott E. Denmark. At UIUC he investigated the transmetalation step in the Suzuki-Miyaura reaction by characterizing pre-transmetalation intermediates.Upon completion of his Ph.D. in 2017 he began his NIH postdoctoral fellowship at Massachusetts Institute of Technology with Prof. Stephen L. Buchwald. At MIT he designed new ligands for copper hydride catalyzed hydroamination reactions by using an combined computationally and experimentally informed process. In the Fall of 2020 Andy joined the chemistry faculty at Texas A&M University as an assistant professor. His research group focuses on using physical organic chemistry to develop new synthetic methods by investigating the chemical reactivity of highly reactive intermediates. Appointment August 2020 – Texas A&M University Assistant Professor, Department of Chemistry Education August 2011 –University of Illinois at Urbana-Champaign May 2017 Ph. D. in Chemistry Thesis: Pre-transmetalation intermediates in the Suzuki-Miyaura reaction revealed: The missing link Advisor: Prof. Scott E. Denmark May 2010 –August 2011 University of North Carolina at Charlotte Masters of Science in Chemistry Thesis: Investigations of Mixed Organocuprates Advisor: Prof. Craig A. Ogle August 2006 –May 2010 University of North Carolina at Charlotte Bachelors of Science in Chemistry Thesis: Investigations of Lithium Tetramethylcuprate Advisor: Prof. Craig A. Ogle Research Experience June 2017 – Massachusetts Institute of Technology June 2020 NIH Postdoctoral Fellow (Advisor: Prof. Stephen L. Buchwald) August 2011 – University of Illinois at Urbana-Champaign May 2017 Graduate Research Assistant (Advisor: Prof. Scott E. Denmark) May 2008 –University of North Carolina at Charlotte August 2011 Graduate / Undergraduate Research Assistant (Advisor: Prof. Craig A. Ogle)

研究领域

We are a synthetic methods group that is focused on understanding and developing new reactions to solve some of the most important challenges in chemistry today, from the asymmetric construction of sp3 stereocenters to the synthesis of complex conjugated polymers. Specifically, we are motivated to develop new reactions for the organic synthesis of bioactive molecules. While most of our investigations involve the development of new transformations that leverage the unique properties of carbanions or organometallic reagents, we are also interested in understanding the underlying principles of chain transfer polymerization reactions. Key to developing new synthetic transformations is obtaining new mechanistic insights that drive their conception. In addition to our mechanism driven methodology development, we also develop and use new NMR techniques as well as devices such as multiple injection NMR (MI-NMR) spectroscopy which allows us to monitor and control the reactivity of transient species inside the NMR probe. Reaction Discovery & Mechanistic Studies Constructive Ozonolysis: C-O Bond Formation Synthesis of Reactive Materials Design of Rapid-Injection NMR Systems

近期论文

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Arriaga, D. K.; Kang, S.; Thomas, A. A. "Solvent Effects on the Rate of Ozonolysis: Development of a Homogeneous Flow Ozonolysis Protocol”. Manuscript Submitted. Wu, D.; Martin, R. T.; Piña, J.; Kwon, J.; Crockett, M. P.; Thomas, A. A.; Gutierrez, O.; Park, N. H.; Hedrick, J. L.; Campos, L. M. “A generalized approach to activate CO2 for carbonation polymerizations and functional transformations”. Manuscript Submitted. Arriaga, D. K.; Thomas, A. A. "Capturing primary ozonides for a syn-dihydroxylation of olefins". Nat. Chem. 2023, https://doi.org/10.1038/s41557-023-01247-5. Crockett, M. P.; Piña, J.; Gogoi, A. R.; Lalisse, R. F.; Nguyen, A. V.; Gutierrez, O.; Thomas, A. A. "Breaking the tert-Butyllithium Contact Ion Pair: A Gateway to Alternate Selectivity in Lithiation Reactions". J. Am. Chem. Soc. 2023, 145, 10743–10755. Crockett, M. P.; Aguirre, L. S.; Jimenez, L. B.; Hsu, H.-H.; Thomas, A. A. "Preparation of Highly Reactive Lithium Metal Dendrites for the Synthesis of Organolithium Reagents". J. Am. Chem. Soc. 2022, 144, 16631-16637. Arriaga, D. K.; Thomas, A. A. "Antibiotics the easy way". Nat. Synth. 2022 (News & Views). Zhukhovitskiy, A. V.; Kobylianskii, I. J.; Thomas, A. A.; Evans, A. M.; Delaney, C. P.; Flanders, N. C.; Denmark, S. E.; Dichtel, W. R.; Toste, F. D. "A Dinuclear Mechanism Implicated in Controlled Carbene Polymerization". J. Am. Chem. Soc. 2019, 141, 6473-6478. Thomas, A. A.; Speck, K.; Kevlishvili, I.; Lu, Z.; Liu, P.; Buchwald, S. L. "Mechanistically Guided Design of Ligands That Significantly Improve the Efficiency of CuH-Catalyzed Hydroamination Reactions". J. Am. Chem. Soc. 2018, 140, 13976- 13984. Thomas, A. A.; Zahrt, A. F.; Delaney, C. P.; Denmark, S. E. "Elucidating the Role of the Boronic Esters in the Suzuki-Miyaura Reaction: Structural, Kinetic, and Computational Investigations". J. Am. Chem. Soc. 2018, 140, 4401-4416. Thomas, A. A.; Denmark, S. E. Ernest L. Eliel, "A Physical Organic Chemist with the Right Tool for the Job: Rapid Injection Nuclear Magnetic Resonance". In Stereochemistry and Global Connectivity: The Legacy of Ernest Eliel; Cheng, H. N., Ed.; ACS Symposium Series; American Chemical Society: Washington, DC, 2017; Vol. 2, pp 105-134. Thomas, A. A.; Wang, H.; Zahrt, A. F.; Denmark, S. E. "Structural, Kinetic, and Computational Characterization of the Elusive Arylpalladium(II)boronate Complexes in the Suzuki-Miyaura Reaction". J. Am. Chem. Soc. 2017, 139, 3805-3821. Thomas, A. A.; Denmark, S. E. "Pre-transmetalation intermediates in the Suzuki-Miyaura reaction revealed: The missing link". Science, 2016, 352, 329-332. Dale, J. E.; Vermeulen, N. A.; Thomas, A. A.; Barnes, J. C.; Juríček, M.; Blackburn, A. K.; Strutt, N. L.; Sarjeant, A. A.; Stern, C. L.; Denmark, S. E.; Stoddart, J. F. "ExCage". J. Am. Chem. Soc. 2014, 136, 10669-10682. Bertz, S. H.; Cope, S. K.; Hardin, R. A.; Murphy, M. D.; Ogle, C. A.; Smith, D. T.; Thomas, A. A.; Whaley, T. N. "Complexes of the Gilman Reagent with Double Bonds across the π−σ Continuum". Organometallics. 2012, 31, 7827-7838. Bertz, S. H.; Browder, K. L.; Hardin, R. A.; Murphy M. D., Ogle, C. A.; Thomas, A. A. "Ligand Exchange in Mixed Organocuprate(I) π-Complexes." Organometallics. 2012, 31, 7809-7811. Bertz, S. H.; Hardin, R. A., Murphy, M. D., Ogle, C. A., Richter, J. D., Thomas, A. A. "Rapid Injection NMR Reveals η3 ‘π−Allyl’ CuIII Intermediates in Addition Reactions of Organocuprate Reagents". J. Am. Chem. Soc. 2012. 134, 9557-9560. Bertz, S. H.; Hardin, H. A.; Murphy, M. D.; Ogle, C. A.; Richter, J. D.; Thomas, A. A. "Minimization of Organocuprate Complexity through Self-Organization: Remarkable Orientation Effect in Mixed Cuprate π Complexes". Angew. Chem. Int. Ed. 2012, 51, 2681-2685. Bertz, S. H.; Moazami, Y.; Murphy, M. D.; Ogle, C. A.; Richter, J. D.; Thomas, A. A. "Complexes of Gilman Reagents with C−S and C−N Double Bonds: σ or π Bonding"? J. Am. Chem. Soc. 2010, 132, 9549-9551. Bertz, S. H.; Murphy, M. D.; Ogle, C. A.; Thomas, A. A. "Organocuprate(III) chemistry: synthesis and reactivity of amido, cyano, phosphido and thiolato ate complexes of copper(III)". Chem. Commun. 2010, 46, 1255-1256. Bartholomew, E. R.; Bertz, S. H.; Cope, S. K.; Murphy, M. D.; Ogle, C. A.; Thomas, A. A. "Serendipity strikes again–efficient preparation of lithium tetramethylcuprate(III) via rapid injection NMR". Chem. Commun. 2010, 46, 1253-1254.