Phone: (970) 491-6782
- Ph. D. The University of Cambridge
Our lab focuses on inventing new synthetic transformations that have multiple applications in the chemical sciences. We are particularly interested in heterocyclic chemistry because of the widespread occurrence of these moieties in pharmaceuticals and agrochemicals. For example, pyridines and diazines are amongst the most common heterocycles in drug compounds, yet the chemistry to directly obtain valuable derivatives from their C–H bonds is underdeveloped.
We have exploited the unique reactivity of main group elements to develop new bond-forming reactions on pyridines and diazines. In this context, organophosphorus compounds are an underexploited class of compounds and reactive intermediates that present numerous new reaction development opportunities. We can synthesize phosphonium salts with precise control of regio- and site-selectivity on a range of azine building blocks and drug-like intermediates and are actively engaged in developing a suite of carbon-carbon and carbon-heteroatom bond formations. Phosphorus ligand-coupling reactions are unusual pathways in this regard that resemble the behavior of late-transition metal complexes. We aim to develop important synthetic transformations for medicinal chemistry, including drug development, radiolabeling, and bioconjugation applications. Recent developments in the group involve exploiting dearomtized pyridine and diazine intermediates as platforms for reaction development.
- Selective Halogenation of Pyridines Using Designed Phosphine Reagents. J. Am. Chem. Soc. 2020, 142, 11295.,
- Non-Symmetrical Bis-Azine Biaryls from Chloroazines: A Strategy Using Phosphorus Ligand-Coupling. J. Am. Chem. Soc. 2019, 141, 15441,
- A Pyridine?Pyridine Cross?Coupling Reaction via Dearomatized Radical Intermediates. Angew. Chem. Int. Ed. 2019, 58, 14882,
- Cobalt-Catalyzed Alkylation of Drug-Like Molecules and Pharmaceuticals Using Heterocyclic Phosphonium Salts ACS Catal. 2019, 9, 4862,
- Heterobiaryl synthesis by contractive C–C coupling via P(V) intermediates. Science, 2018, 362, 799,
- A Unified Approach to Couple Aromatic Heteronucleophiles to Azines and Pharmaceuticals. Angew. Chem. Int. Ed. 2018, 57, 12514,
- Site-Selective Switching Strategies to Functionalize Polyazines. J. Am. Chem. Soc. 2018, 140, 8020,
- A General Strategy for Site-Selective Incorporation of Deuterium and Tritium into Pyridines, Diazines and Pharmaceuticals. J. Am. Chem. Soc. 2018, 140, 1990,
- Phosphonium Salts as Pseudohalides: Regioselective Nickel-Catalyzed Cross-Coupling of Complex Pyridines and Diazines. Angew. Chem. Int. Ed. 2017, 56, 9833-9836,
- Selective Functionalization of Pyridines via Heterocyclic Phosphonium Salts. J. Am. Chem. Soc. 2016, 138, 13806-13809,