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Abigail Doyle

Research Focus


The synthesis of both natural and unnatural organic compounds in optically active form constitutes a central challenge in chemistry, especially in relation to the production of bioactive compounds and novel materials. In order to contribute to these studies, we invent new tools for synthesis through the design of chiral catalysts and widely applicable catalytic strategies to effect chemo- and stereoselective transformations. Our research aims to elucidate reactivity principles of organic and organometallic catalysis and to reduce the environmental impact of synthetic organic chemistry through the identification of practical and efficient methods.

The problems that we choose to address provide routes to complex organic architectures from readily available and inexpensive feedstock chemicals. In the past year, we have pursued three areas within this program: (1) the invention of new catalytic reaction methods for the synthesis of fluorinated compounds using nucleophilic fluorine sources; (2) the development of transition metal-catalyzed C–C bond-forming reactions with epoxides, aziridines, and N-containing aromatic compounds; and (3) the design of chiral hemilabile phosphine ligands of broad utility for enantioselective catalysis.

Projects in the group are designed to provide students with expertise in reaction discovery and development, while exposing them to problems in complex target synthesis and mechanistic analysis.

Selected Recent Publications

  • Braun, M.-G.; Doyle, A. G. Palladium-Catalyzed Allylic C–H Fluorination. J. Am. Chem. Soc. 2013, 135, 12990–12993.
    Highlighted in:
    • Ritter, S. K. Olefins Easily Flagged with Fluorine. C&ENews 2013, 91, 42.
    • Top most downloaded article in JACS in August & September
  • Braun, M.-G.; Katcher, M. H.; Doyle, A. G. Carbofluorination via a Palladium-Catalyzed Cascade Reaction. Chemical Science, 2013, 4, 1216–1220.
    Highlighted in:
    • Top ten most downloaded articles for January–March 2013.
  • Kalow, J. A.; Schmitt, D. E.*; Doyle, A. G. Synthesis of b-Fluoroamines by Lewis Base-Catalyzed Hydrofluorination of Aziridines. J. Org. Chem. 2012, 77, 4177–4183.
    Highlighted in:
    • Top ten most downloaded articles for April and May 2012
    • Undergraduate co-author
  • Huang, C.-Y. (Dennis); Doyle, A. G. Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines. J. Am. Chem. Soc. 2012, 134, 9541–9544.
    Highlighted in:
    • Top ten most downloaded articles for March and April 2012
    • Selected by the JACS editors for the cover issue and as a Spotlight article (DOI: 10.1021/ja3050647)
    • Synfacts 2012, 8, 1018
  • Graham, T. J. A.; Doyle, A. G. Nickel-Catalyzed Cross Coupling of Chromene Acetals and Boronic Acids. Org. Lett. 2012, 14, 1616–1619.
    Highlighted in:
    • Top ten most downloaded articles for February 2012
    • McLaughlin, M.; Widegren, M.; Paul, S.; Ramirez, A.; Richardson, P.; Zlota, A.; Laird, T. Some Items of Interest to Process R&D Chemists and Engineers. Org. Proc. Res. Dev. 2012, 16, 716–726.
  • Katcher, M. H.; Sha, A.; Doyle, A. G. Regio- and Enantioselective Fluorination of Acyclic Allylic Halides. J. Am. Chem. Soc. 2011, 133, 15902–15905.
    Highlighted in:
    • Top ten most downloaded articles for September 2011
    • Palladium-Catalyzed Enantioselective Fluorination of Allylic Halides. Synfacts 2011, 1316.
  • Graham, T. J. A.; Doyle, A. G. Transition Metal-Catalyzed Cross Coupling with N-Acyliminium Ions Derived from Quinolines and Isoquinolines. Chem. Sci. 2011, 2, 980–984.
    Highlighted in:
    • Top ten most downloaded articles for February, March, April, and May 2011
  • Shaw, T. W.; Kalow, J. A.; Doyle, A. G. Fluoride ring-opening kinetic resolution of terminal epoxides: preparation of (S)-2-fluoro-1-phenylethanol. Org. Syn. 2012, 89, 9–18.
    Highlighted in:
    • Selected by the Editorial Board as the “Featured Article” on the Organic Syntheses homepage
  • Katcher, M. H.; Doyle, A. G. Palladium-Catalyzed Asymmetric Synthesis of Allylic Fluorides. J. Am. Chem. Soc. 2010, 132, 17402–17404.
    Highlighted in:
    • McLaughlin, M.; Wilson, I.; Delaney, P.; Zhao, W.; Zlota, A.; Laird, T. Some Items of Interest to Process R&D Chemists and Engineers. Org. Proc. Res. Dev. 2011, 15, 306–313.
    • Top ten most downloaded articles for 12 months following publication in JACS
  • Kalow, J. A.; Doyle, A. G. Enantioselective Ring-Opening of Epoxides by Fluoride Anion Promoted by a Cooperative Dual Catalyst System. J. Am. Chem. Soc. 2010, 132, 3268–3269.
    Highlighted in:
    • McLaughlin, M.; Garcia Rubio, S.; Wilson, I.; Zhao, W.; Laird, T.; Zlota, A. Some Items of Interest to Process R&D Chemists and Engineers. Org. Proc. Res. Dev. 2010, 14, 750–758.
    • Asymmetric Synthesis of Fluorohydrins. Synfacts 2010, 673.
    • Enantioselective Ring Opening of Epoxides by Fluoride Anion. Synform 2010, A58.
    • Top ten most downloaded articles for February, March, and April 2010

Abigail Doyle

Doyle Lab Webpage
agdoyle@princeton.edu
Frick Laboratory, 129
Phone: 609-258-3900

Faculty Assistant:
Clarice Gethers
cgethers@princeton.edu
Frick Laboratory, 221
Phone: 609-258-0355