Doyle, Abigail


WebsiteHome URL
Division
Organic
Title
Faculty
Professor
Specialties
Organic Synthesis
Organometallic Chemistry
Catalysis
Physical Organic Chemistry
Data Science

Contact Information

Email
Office
1505A Molecular Science Building
TBA

Short Biography

Abigail Doyle received her A.B. and A.M. summa cum laude in Chemistry and Chemical Biology from Harvard University in 2002 and her PhD from the same department in 2008. Professor Doyle began her independent academic career in the Department of Chemistry at Princeton University in 2008. In 2021, she moved to UCLA as the Saul Winstein Chair in Organic Chemistry. 

Research Interests

The Doyle lab conducts research at the interface of organic, organometallic, physical organic, and computational chemistry. Our goal is to address unsolved problems in organic synthesis through the development of catalysts, catalytic reactions, and synthetic methods. We apply mechanistic and computer-assisted techniques to the analysis of these reactions in order to uncover general principles that can guide the design of improved catalysts and the discovery of new reactions. Particular areas of interest include

  1. Ni-catalyzed cross coupling
  2. nucleophilic fluorination and radiofluorination
  3. photocatalysis
  4. machine learning for chemical synthesis

UCLA Chemistry Doyle Group

 

Honors & Awards

  • American Chemical Society Fellow (2020)
  • RSC Fluorine Award (2019)
  • 15th Hirata Prize (2019)
  • BMS Unrestricted Grant in Synthetic Organic Chemistry (2016)
  • Phi Lambda Upsilon National Fresenius Award (2014)
  • Presidential Early Career Award for Scientists and Engineers (2014)
  • Novartis Chemistry Lectureship (2014/2015)
  • Bayer Excellence in Science Award (2013)
  • Arthur C. Cope Scholar Award (2013)
  • Camille-Dreyfus Teacher Scholar Award (2013)
  • Amgen Young Investigator Award (2012)
  • Alfred P. Sloan Foundation Fellowship (2012)
  • NSF CAREER Award (2012-2017)

Publications

[ SELECTED RECENT PUBLICATIONS ]

  • Shen, Y.; Borowski, J. E.; Hardy, M. A.; Sarpong, R.; Doyle, A. G.; Cernak, T. “Automation and computer-assisted planning for chemical synthesis.” Nat. Rev. Methods Primers 2021, 1, 23.
     
  • Shields, B. J.; Stevens, J.; Li, J.; Parasram, M.; Damani, F.; Martinez-Alvarado, J.; Janey, J.; Adams, R. P.; Doyle, A. G. Bayesian Reaction Optimization as a Tool for Chemical Synthesis. Nature 2021, 590, 89–96.
     
  • Kariofillis, S. K.; Doyle, A. G.  “Synthetic and Mechanistic Implications of Chlorine Photoelimination in Nickel/Photoredox C(sp3)–H Cross-Coupling.”  Acc. Chem. Res. 2021, 54, 988–1000.
     
  • Webb, E. W.; Park, J. B.; Cole, E. L.; Donnelly, D. J.; Bonacorsi, S. J.; Ewing, W. R.; Doyle, A. G. “Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis.” J. Am. Chem. Soc. 2020, 142, 9493–9500.
     
  • Estrada, J. G.; Young, W. L.; Ting, S. I.; Doyle, A. G. “Role of Electron-Deficient Olefin Ligands in a Ni-Catalyzed Aziridine Cross Coupling to Generate Quaternary Carbons.” J. Am. Chem. Soc. 2020, 142, 8928–8937.
     
  • Kariofillis, S. K.; Shields, B. J.; Tekle-Smith, M. A.; Zacuto, M. J.; Doyle, A. G. “Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source.” J. Am. Chem. Soc. 2020, 142, 7683–7689.
     
  • Steiman, T. J.; Liu, J.; Mengiste, A.; Doyle, A. G. “Synthesis of β-Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides.” J. Am. Chem. Soc. 2020, 142, 7598–7605.
     
  • Ting, S. I.; Garakyaraghi, S.; Taliaferro, C. M.; Scholes, G. D.; Castellano, F. N.; Doyle, A. G. “Excited States of Ni Complexes Relevant to Photoredox Catalysis: Characterization and Mechanistic Implications.” J. Am. Chem. Soc. 2020, 142, 5800–5810.
     
  • Stache, E. E.; Ertel, A. B.; Rovis, T.; Doyle, A. G. C–O Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage-Independent Activation of Strong C–O Bonds. ACS Catalysis 2018, 8, 11134–11139.
     
  • Ackerman, L. K. G.; Martinez Alvarado, J. I.; Doyle, A. G. Direct C–C Bond Formation from Alkanes Using Ni-Photoredox Catalysis. J. Am. Chem. Soc. 2018, 140, 14059–14063.
     
  • Nielsen, M. K.; Ahneman, D. T.; Riera, O.; Doyle, A. G. Deoxyfluorination with Sulfonyl Fluorides: Navigating Reaction Space with Machine Learning. J. Am. Chem. Soc. 2018, 140, 5004–5008.
     
  • Ahneman, D. T.; Estrada, J. G.; Lin, S.; Dreher, S. D.; Doyle, A. G. Predicting reaction performance in C–N cross-coupling using machine learning. Science 2018, 360, 186–190.
     
  • Heinz, C.; Lutz, J. P.; Simmons, E. M.; Miller, M. M.; Ewing, W. R.; Doyle, A. G. Ni-Catalyzed Carbon–Carbon Bond-Forming Reductive Amination. J. Am. Chem. Soc. 2018, 140, 2292–2300.
     
  • Woods, B. P.; Orlandi, M.; Huang, C.-Y. Sigman, M. H.; Doyle, A. G. “Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines” J. Am. Chem. Soc. 2017, 139, 5688–5691.
     
  • Wu, K.; Doyle, A. G. “Parameterization of phosphine ligands demonstrates enhancement of nickel catalysis via remote steric effects” Nature Chem. 2017, 9, 779–784.
     
  • Shields, B. J.; Doyle, A. G. Direct C(sp3)−H Cross Coupling Enabled by Catalytic Generationof Chlorine Radicals. J. Am. Chem. Soc. 2016, 138, 12719–12722.
     
  • Nielsen, M. K.; Ugaz, C. R.; Li, W.; Doyle, A. G. PyFluor: A Low-Cost, Stable, and Selective Deoxy-fluorination Reagent. J. Am. Chem. Soc. 2015, 137, 9571−9574.
     
  • Huang, C.-Y.; Doyle, A. G. Electron-Deficient Olefin Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed Cross Coupling. J. Am. Chem. Soc. 2015, 137, 5638–5641.
     
  • Shields, J. D.; Gray, E. E.; Doyle, A. G. A Modular, Air-Stable Nickel Precatalyst. Org. Lett. 2015, 17, 2166–2169.
     
  • Zuo, Z.; Ahneman, D.; Chu, L.; Terrett, J.; Doyle, A. G.; MacMillan, D. W. C. Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp3-carbons with aryl halides. Science 2014, 345, 437–440.
     
  • Graham, T. J. A.; Lambert, R. F.; Ploessl, K.; Kung, H. F.; Doyle, A. G. Enantioselective radiosynthesis of positron emission tomography (PET) tracers containing [18F]fluorohydrins. J. Am. Chem. Soc. 2014, 136, 5291–5294.
     
  • Braun, M.-G.; Doyle, A. G. Palladium-Catalyzed Allylic C–H Fluorination. J. Am. Chem. Soc. 2013, 135, 12990–12993.
     
  • Sylvester, K. T.; Wu, K.; Doyle, A. G. Mechanistic Investigations of the Nickel-Catalyzed Suzuki Reaction of N,O-Acetals: Evidence for Boronic Acid-Assisted Oxidative Addition and an Iminium Activation Pathway. J. Am. Chem. Soc. 2012, 134, 16967–16970.
     
  • Huang, C.-Y. (Dennis); Doyle, A. G. Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines. J. Am. Chem. Soc. 2012, 134, 9541–9544.
     
  • Katcher, M. H.; Sha, A.; Doyle, A. G. Regio- and Enantioselective Fluorination of Acyclic Allylic Halides. J. Am. Chem. Soc. 2011, 133, 15902–15905.
     
  • Kalow, J. A.; Doyle, A. G. Mechanistic Investigations of Cooperative Catalysis in the Enantioselective Fluorination of Epoxides. J. Am. Chem. Soc. 2011, 133, 16001–16012.
     
  • Katcher, M. H.; Doyle, A. G. Palladium-Catalyzed Asymmetric Synthesis of Allylic Fluorides. J. Am. Chem. Soc. 2010, 132, 17402–17404.
     
  • 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.