McNally, Andy - Colorado State University

个人简介

Andy attended the University of Cambridge, where he graduated with first class honors in 2003 earned an M.A. and M. Sci. in Natural Sciences with a final year project in Professor Ian Paterson's laboratory working on aldol coupling of Pelouroside A. He continued on to obtain his Ph. D. in 2007 with Dr. Matthew J. Gaunt working on a novel organocatalytic [2,3]-Wittig rearrangement using secondary amines as catalysts. Andy moved to the US as a Marie Curie International Fellow to Professor David W. C. MacMillan's at Princeton University. There, he developed the concept of 'accelerated serendipity' where high-throughput screening methods were used to discover new chemical reactions. A photoredox process that coupled amines with cyanoaromatics to make benzylic amines was discovered using this approach. Andy returned to the University of Cambridge for a second Postdoc with Matthew Gaunt and developed palladium catalyzed methods to activate aliphatic amines via 4-membered ring palladacycle intermediates. Currently, Andy is an Assistant Professor of Chemistry at Colorado State University in Fort Collins, Colorado.

研究领域

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.

近期论文

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A deconstruction-reconstruction strategy for pyrimidine diversification: B. J. H. Uhlenbruck, C. M. Josephitis, L. D. Lescure, R. Paton, and A. McNally, Nature, 2024. Synthesis of 15N-Pyridines and Higher Mass Isotopologs via Zincke Imine Intermediates: H. M. H. Nguyen,* D. C. Thomas,* M. A. Hart,† K. R. Steenback,† J. N. Levy, and A. McNally. J. Am. Chem. Soc. 2024, 146, 5, 2944. A General Strategy for N–(Hetero)aryl Piperidine Synthesis Using Zincke Imine Intermediates: J. D. Selingo,* J. W. Greenwood,* M. K. Andrews, C. Patel, A. J. Neel, B. Pio, M. Shevlin, E. M. Phillips, M. L. Maddess, A. McNally. J. Am. Chem. Soc. 2024, 146, 1, 936. Late-Stage C–H Functionalization of Azines: C. M. Josephitis,* H. M. H. Nguyen,* A. McNally. Chem. Rev. 2023, 123, 12, 7655. Halogenation of the 3-position of pyridines through Zincke imine intermediates: B. T. Boyle,* J. N. Levy,* L. D. Lescure, R. S. Paton, A. McNally. Science, 2022, 378, 773. Featured in: C&EN Previously on ChemRxiv. 4-Selective Pyridine Alkylation via Wittig Olefination of Dearomatized Pyridylphosphonium Ylides: P. J. Fricke, R. D. Dolewski, A. McNally, Angew. Chem. Int. Ed., 2021, 60, 1. Phosphorus-Mediated sp2-sp3 Couplings for Selective C–H Fluoroalkylation of Complex Azines: X. Zhang,* K. G. Nottingham,* C. Patel, J. V. Alegre-Requena, J. N. Levy, R. S. Paton, A. McNally, Nature, 2021, 594, 217. Pyridylphosphonium Salts as Alternatives to Cyanopyridines in Radical-Radical Coupling Reactions: J. W. Greenwood, B. T. Boyle, A. McNally, Chem. Sci., 2021, 12, 10538. Facile Pyridine SNAr Reactions via N-Phosphonium-Pyridinium Intermediates: B.T. Boyle, J. L. Koniarczyk, A. McNally, Synlett, 2021, 32, 215