M.S., Organic Chemistry, The University of Chicago, 2011
B.A. Chemistry and Biology, St. Mary's College of Maryland, 2010
Research Program Overview:
Chemical catalysis is one of the most powerful tools available in organic chemistry. The unique ability of a catalyst to control reactivity, form unstable intermediates in situ, and override inherent chemical selectivity makes catalyst development an exciting area of chemical research. Moreover, catalysts offer access to molecular scaffolds which would be either challenging or impossible to synthesize through traditional means. Our group is interested in investigating various catalyst systems and applying these molecular catalysts to synthesize complex and biologically interesting synthetic targets. Our group consists of both graduate and undergraduate researchers working on a variety of projects.
I am particularly interested in the use of phosphines, and their related compounds, for use as organic catalysts. Organocatalysis is an exciting area of chemical research which involves the use of non-transition metal elements to promote new catalyzed reactions. These reactions can achieve high levels of chemo-, diastero- and enantioselectivity using earth abundant compounds to mediate and control the reaction. Phosphine is of particular interest to our group as its low basicity and selective nucleophilicity allows for the covalent activation of target molecules. Along with developing novel applications for phosphine organocatalysts we are looking to incorporate them into modular molecular scaffolds taking inspiration from how nature uses enzymes to achieve exquisite reactivity.
First Row Transition Metals:
The second and third row transition metals, such as palladium, platinum, gold, rhodium, iridium and ruthenium are widely used in both academic labs and industrial plants. They possess reliable reactivity patterns and have fundamentally changed how synthetic chemists think about constructing molecules. However, these metals are a limited resource, existing in only trace amounts in the earth's crust. In order to address the growing need to move away from these trace elements our group is interested in using the far more abundant first row metals to synthesize compounds which were previously only accessible through use of precious metal catalysts. Being less harmful to mine and being less costly such efforts will appeal to both environmental groups and industry. Furthermore, first row metals can offer different reactivity patterns which will allow for the development of orthogonal methods to what is currently known.
Zarcone, S. R.; Yarbrough, H. J.; Neal, M. J.; Kelly, J. C.; Kaczynski, K. L.; Bloomfield, A. J.; Bowers, G. M.; Montgomery, T. D.; Chase, D. T., Synthesis and photophysical properties of nitrated aza-BODIPYs. New J. Chem. 2022, 46 (9), 4483-4496.
Neal, M. J.; Hejnosz, S. L.; Rohde, J. J.; Evanseck, J. D.; Montgomery, T. D., Multi-Ion Bridged Pathway of N-Oxides to 1,3-Dipole Dilithium Oxide Complexes. The Journal of Organic Chemistry 2021, 86 (17), 11502-11518.
Montgomery, T. D.; Smith, A. B. III "α-Silyl Amides: Effective Bifunctional Lynchpins for Type I Anion Relay Chemistry" Org. Lett. 2017, 19 (22), 6216-6219.
Rombola, M.; Sumaria, C. S.; Montgomery, T. D.; Rawal, V. H. "Development of Chiral, Bifunctional Thiosquaramides: Enantioselective Michael Additions of Barbituric Acids to Nitroalkenes" J. Am. Chem. Soc. 2017, 139, 5297-5300.
Montgomery, T. D.; Rawal, V. H. "Palladium-Catalyzed Modular Synthesis of Substituted Piperazines and Related Nitrogen Heterocycles" Org. Lett. 2016, 18, 740-743.
-Selected for Synfacts Highlights: Synfacts 2016, 12, 342.
Nibbs, A. E.; Montgomery, T. D.; Zhu, Y.; Rawal, V. H. "Access to Spirocyclized Oxindoles and Indolenines via Palladium-Catalyzed Cascade Reactions of Propargyl Carbonates with 2-Oxotryptamines and Tryptamines." J. Org. Chem. 2015, 80, 4928-4941.
Montgomery, T. D.; Nibbs, A. E.; Zhu, Y.; Rawal, V. H. "Rapid Access to Spirocyclized Indolenines via Palladium-Catalyzed Cascade Reactions of Tryptamine Derivitives and Propargyl Carbonate." Org. Lett. 2014, 16, 3480-3483.
Montgomery, T. D.; Ye, Z.; Kagawa, N.; Rawal, V. H. "Palladium-Catalyzed Decarboxylative Allylation and Benzylation of N-Alloc and N-Cbz Indoles." Org. Lett. 2013, 15, 1140-1143.
Prakash, G. K. S.; Shao, N.; Wang, F.; Ni, C. (Checkers: Montgomery, T. D., Rawal, V. H.) "Preparation of α-Fluororbis(phenylsulfonyl)methane (FBSM) Org. Synth. 2013, 90, 130-144.