
Website | Home URL |
Division | Organic |
Title |
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Specialties |
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agdoyle@chem.ucla.edu | |
Office | 1505A Molecular Science Building |
Office Phone | 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 to uncover general principles that can guide the design of improved catalysts and the discovery of new reactions.
Honors & Awards
- MAVEN Senior Scientist (2024)
- 2023 OMCOS Award XXI
- 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)
Representative Publications
For the full list, please visit here.
- LeSueur, A.; Tao, N.; Doyle, A.G.; Sigman, M. “Multi-Threshold Analysis for Chemical Space Mapping of Ni-Catalyzed Suzuki-Miyaura Couplings” J. Org. Chem., 2024, e202400428
- Sedillo, K.; Fan, F.; Knowles, R. R.; Doyle, A. G. “Cooperative Phosphine-Photoredox Catalysis Enables N–H Activation of Azoles for Intermolecular Olefin Hydroamination” J. Am. Chem. Soc. 2024, 146, 20349-20356.
- Cusumano, A. Q; Chaffin, B. C.; Doyle, A. G. “Mechanism of Ni-Catalyzed Photochemical Halogen Atom-Mediated C(sp3)–H Arylation” J. Am. Chem. Soc. 2024, 146, 15331-15344.
- Sheng, H.; Sun, J.; Rodríguez, O.; Hoar, B. B.; Zhang, W.; Xiang, D.; Tang, T.; Hazra, A.; Min, D. S.; Doyle, A. G.; Sigman, M. S.; Costentin, C.; Gu, Q.; Rodríguez-López, J.; Liu, C. “Autonomous closed-loop mechanistic investigation of molecular electrochemistry via automation” Nat. Commun. 2024, 15, 2781.
- Romer, N. P.; Min, D. S.; Wang, J. Y.; Walroth, R. C.; Mack, K. A.; Sirois, L. E.; Gosselin, F.; Zell, D.; Doyle, A. G.; Sigman, M. S. “Data Science Guided Multiobjective Optimization of a Stereoconvergent Nickel-Catalyzed Reduction of Enol Tosylates to Access Trisubstituted Alkenes” ACS Catal, 2024, 14, 4699-4708.
- Wang, J. Y.; Stevens, J. M.; Kariofillis, S. K.; Tom, M.-J.; Golden, D. L.; Li, J.; Tabora, J. E.; Parasram, M.; Shields, B. J.; Primer, D. N.; Hao, B.; Del Valle, D.; DiSomma, S.; Furman, A.; Zipp, G. G.; Melnikov, S.; Paulson, J.; Doyle, A. G. “Identifying general reaction conditions by bandit optimization” Nature, 2024, 626, 1025-1033.
- Lyons, T. W.; Leibler, I. N.-M.; He, C. Q.; Gadamsetty, S.; Estrada, G. J.; Doyle, A. G. “Broad Survey of Selectivity in the Heterogeneous Hydrogenation of Heterocycles” J. Org. Chem. 2024, 89, 1438-1445.
- Newman-Stonebraker, S. H.; Raab, T. J.; Doyle, A. G. “Catalyst Deactivation of a Monoligated CyJohnPhos-Bound Nickel(0) Complex” Organometallics 2023, 42, 3438-3441.
- Raghavan, P; Haas, B. C.; Ruos, M. E.; Schleinitz, J; Doyle, A. G.; Reisman, S. E.; Sigman, M. S.; Coley, C. W. “Dataset Design for Building Models of Chemical Reactivity” ACS Cent. Sci. 2023, 9, 2196-2204.
- Williams, W. L.; Gutiérrez-Valencia, N. E.; Doyle, A. G. “Branched-Selective Cross-Electrophile Coupling of 2-Alkyl Aziridines and (Hetero)aryl Iodides Using Ti/Ni Catalysis” J. Am. Chem. Soc. 2023, 145, 24175-24183.
- Newman-Stonebraker, S. H.; Raab, T. J.; Roshandel, H. R.; Doyle, A. G. “Synthesis of Nickel(I)–Bromide Complexes via Oxidation and Ligand Displacement: Evaluation of Ligand Effects on Speciation and Reactivity” J. Am. Chem. Soc. 2023, 145, 19368-19377.
- Ruos, M. E.; Kinney, R. G.; Ring, O. T.; Doyle, A. G. “A General Photocatalytic Strategy for Nucleophilic Amination of Primary and Secondary Benzylic C–H Bonds” J. Am. Chem. Soc. 2023, 145, 18487-18496.
- Dunlap, J. H.; Ethier, J. G.; Putnam-Neeb, A. A.; Iyer, S.; Luo, S.-X. L.; Feng, H.; Torres, J. A. G.; Doyle, A. G.; Swager, T. M.; Vaia, R. A.; Mirau, P.; Crouse, C. A.; Baldwin, L. A. “Continuous flow synthesis of pyridinium salts accelerated by multi-objective Bayesian optimization with active learning” Chem. Sci. 2023, 14, 8061-8069.
- Borowski, J. E.; Newman-Stonebraker, S. H.; Doyle, A. G. “Comparison of Monophosphine and Bisphosphine Precatalysts for Ni-Catalyzed Suzuki–Miyaura Cross-Coupling: Understanding the Role of the Ligation State in Catalysis” ACS. Catal. 2023, 13, 7966-7977.
- Leibler, I. N.-M.; Gandhi, S. S.; Tekle-Smith, M. A.; Doyle, A. G. “Strategies for Nucleophilic C(sp3)–(Radio)Fluorination” J. Am. Chem. Soc. 2023, 145, 9928-9950.
- Tang, T.; Hazra, A.; Min D. S.; Williams W. L.; Doyle A. G.; Sigman M. S. “Interrogating the Mechanistic Features of Ni(I)-Mediated Aryl Iodide Oxidative Addition Using Electroanalytical and Statistical Modeling Techniques” J. Am. Chem. Soc. 2023, 145, 8689-8699.
- Żurański, A. M.; Gandhi, S. S.; Doyle, A. G. “A Machine Learning Approach to Model Interaction Effects: Development and Application to Alcohol Deoxyfluorination” J. Am. Chem. Soc. 2023, 145, 7898–7909.
- Saebi, M.; Nan, B.; Herr, J. E.; Wahlers, J.; Guo, Z.; Zurański, A. M.; Kogej, T.; Norrby, P.-O.; Doyle, A. G.; Wiest, O.; Chawla, N. V. “On the Use of Real-World Datasets for Reaction Yield Prediction” Chem. Sci. 2023.
- Murray, P. R. D.; Leibler, I. N.-M.; Hell, S. M.; Villalona, E.; Doyle, A. G.; Knowles, R. R. “Radical Redox Annulations: A General Light-Driven Method for the Synthesis of Saturated Heterocycles” ACS Catal. 2022, 12, 13732-13740.
- Torres, J. A. G.; Lau, S. H.; Anchuri, P.; Stevens, J. M.; Tabora, J. E.; Li, J.; Borovika, A.; Adams, R. P.; Doyle, A. G. “A Multi-Objective Active Learning Platform and Web App for Reaction Optimization” J. Am. Chem. Soc. 2022, 144, 19999–20007.
- Dongbang, S; Doyle, A. G. “Ni/Photoredox-Catalyzed C(sp3)–C(sp3) Coupling between Aziridines and Acetals as Alcohol-Derived Alkyl Radical Precursors” J. Am. Chem. Soc. 2022, 144, 20067–20077.
- Newman-Stonebraker, S. H.; Wang, J. Y.; Jeffrey P. D.; Doyle, A. G. “Structure–Reactivity Relationships of Buchwald-Type Phosphines in Nickel-Catalyzed Cross-Couplings” J. Am. Chem. Soc. 2022, 144, 19635-19648.
- Millet, A.; Cesana, P. T.; Sedillo, K.; Bird, M. J.; Schlau-Cohen, G. S.; Doyle, A. G.; MacMillan, D. W. C.; Scholes, G. D. “Bioinspired Supercharging of Photoredox Catalysis for Applications in Energy and Chemical Manufacturing.” Acc. Chem. Res. 2022, 55, 1423-1434.
- Ting, S. I.; Williams, W. L.; Doyle, A. G. “Oxidative Addition of Aryl Halides to a Ni(I)-Bipyridine Complex.” J. Am. Chem. Soc. 2022, 144, 5575-5582.
- Żurański, A. M.; Wang, J. Y.; Shields, B. J.; Doyle, A. G. “Auto-QChem: an automated workflow for the generation and storage of DFT calculations for organic molecules.” React. Chem. Eng. 2022, 7, 1276-1284.
- Kariofillis, S. K.; Jiang, S.; Żurański, A. M.; Gandhi, S. S.; Martinez Alvarado, J. I.; Doyle, A. G. “Using Data Science to Guide Aryl Bromide Substrate Scope Analysis in a Ni/Photoredox-Catalyzed Cross-Coupling with Acetals as Alcohol-Derived Radical Sources.” J. Am. Chem. Soc. 2022, 144, 1045-1055.
- Leibler, I. N.-M.; Tekle-Smith, M. A.; Doyle, A. G. “A General Strategy for C(sp3)–H Functionalization with Nucleophiles Using Methyl Radical as a Hydrogen Atom Abstractor.” Nat. Commun. 2021, 12, 6950.
- Cesana, P. T.; Li, B. X.; Shepard, S. G.; Ting, S. I.; Hart, S. M.; Olson, C. M.; Martinez Alvarado, J. I.; Son, M.; Steiman, T. J.; Castellano, F. N.; Doyle, A. G.; MacMillan, D. W. C.; Schlau-Cohen, G. S. “A Biohybrid Strategy for Enabling Photoredox Catalysis with Low-Energy Light.” Chem. 2021, 8, 174-185.
- Kearnes, S. M.; Maser, M. R.; Wleklinski, M.; Kast, A.; Doyle, A. G.; Dreher, S. D.; Hawkins, J. M.; Jensen, K. F.; Coley, C. W. “The Open Reaction Database.” J. Am. Chem. Soc. 2021, 143, 18820-18826.
- Williams, W. L.; Zeng, L.; Gensch, T.; Sigman, M. S.; Doyle, A. G.; Anslyn, E. V. “The Evolution of Data-Driven Modeling in Organic Chemistry.” ACS Cent. Sci. 2021, 7, 1622-1637.
- Chinn, A. J.; Sedillo, K.; Doyle, A. G. “Phosphine/Photoredox Catalyzed Anti-Markovnikov Hydroamination of Olefins with Primary Sulfonamides via α-Scission from Phosphoranyl Radicals.” J. Am. Chem. Soc. 2021, 143, 18331-18338.
- Newman-Stonebraker, S. H.; Smith, S. R.; Borowski, J. E.; Peters, E.; Gensch, T.; Johnson, H. C.; Sigman, M. S.; Doyle, A. G. “Univariate classification of phosphine ligation state and reactivity in cross-coupling catalysis.” Science 2021, 374, 301-308.
- Lau, S. H.; Borden, M. A.; Steiman, T. J.; Parasram, M.; Wang, L. S.; Doyle, A. G. “Ni/Photoredox-Catalyzed Enantioselective Cross-Electrophile Coupling of Styrene Oxides with Aryl Iodides.” J. Am. Chem. Soc 2021, 143, 15873-15881.
- Żurański, A. M.; Martinez Alvarado, J. I.; Shields, B. J.; Doyle, A. G. “Predicting Reaction Yields via Supervised Learning.” Acc. Chem. Res 2021, 54, 1856-1865.
- 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.