Doyle, Abigail - University of California, Los Angeles - Department of Chemistry & Biochemistry

个人简介

Abigail Doyle was born in Princeton, NJ in 1980. She received her A.B. and A.M. summa cum laude in Chemistry and Chemical Biology from Harvard University in 2002. As an undergraduate, she investigated iron-catalyzed epoxidations of alkenes in collaboration with Dr. Christina White. She began her graduate studies at Stanford University working with Professor Justin Du Bois. In 2003, she transferred to Harvard University and joined the laboratory of Professor Eric Jacobsen. Her graduate research included the discovery of a transition metal-catalyzed enantioselective alkylation of tributyltin enolates with alkyl halides and the development of a thiourea catalyst for enantioselective nucleophilic additions to prochiral oxocarbenium ions. Abby began her independent career at Princeton University in 2008 and was promoted to Associate Professor in 2013, before moving to UCLA in 2021 where she is currently the Saul Winstein Chair in Organic Chemistry. EDUCATION 2003-2008 Harvard University, Department of Chemistry and Chemical Biology Degree awarded: Ph.D., NDSEG, NSF, and Harvard Merit Pre-Doctoral Fellow Research Advisor: Professor Eric N. Jacobsen “Engaging Alkyl Halides and Oxocarbenium Ions in Asymmetric Catalysis” 2002-2003 Stanford University, Department of Chemistry NDSEG Pre-Doctoral Fellow Research Advisor: Professor Justin Du Bois 1998-2002 Harvard University, Department of Chemistry and Chemical Biology Degree awarded: A.B. and A.M. with Highest Honors, summa cum laude Research Advisor (2000-2002): Professor Eric N. Jacobsen

研究领域

The Doyle lab conducts research at the interface of organic, organometallic, and physical organic chemistry, enhanced by the use of modern data science and machine learning tools. Our goal is to address unsolved problems in organic synthesis through the development of novel catalysts, catalytic reactions, and synthetic methods. We implement mechanistic and computer-assisted techniques to uncover general chemical principles, predict unseen reactivity, and discover new reactions.

近期论文

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“Strategies for Nucleophilic C(sp3)–(Radio)Fluorination” Leibler, I. N.-M.; Gandhi, S. S.; Tekle-Smith, M. A.; Doyle A. G. J. Am. Chem. Soc. 2023. [DOI: 10.1021/jacs.3c01824] “Interrogating the Mechanistic Features of Ni(I)-Mediated Aryl Iodide Oxidative Addition Using Electroanalytical and Statistical Modeling Techniques” Tang, T.; Hazra, A.; Min D. S.; Williams W. L.; Doyle A. G.; Sigman M. S. J. Am. Chem. Soc. 2023, 145, 8689-8699. [DOI: 10.1021/jacs.3c01726] “A Machine Learning Approach to Model Interaction Effects: Development and Application to Alcohol Deoxyfluorination” Żurański, A. M.; Gandhi, S. S.; Doyle, A. G. J. Am. Chem. Soc. 2023, 145, 7898–7909. [DOI: 10.1021/jacs.2c13093] “On the Use of Real-World Datasets for Reaction Yield Prediction” 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. Chem. Sci. 2023 [DOI: 10.1039/d2sc06041h] “Radical Redox Annulations: A General Light-Driven Method for the Synthesis of Saturated Heterocycles” Murray, P. R. D.; Leibler, I. N.-M.; Hell, S. M.; Villalona, E.; Doyle, A. G.; Knowles, R. R. ACS Catal. 2022, 12, 13732-13740. [DOI: 10.1021/acscatal.2c04316] “A Multi-Objective Active Learning Platform and Web App for Reaction Optimization” 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. J. Am. Chem. Soc. 2022, 144, 19999–20007. [DOI: 10.1021/jacs.2c08592] “Ni/Photoredox-Catalyzed C(sp3)–C(sp3) Coupling between Aziridines and Acetals as Alcohol-Derived Alkyl Radical Precursors” Dongbang, S; Doyle, A. G. J. Am. Chem. Soc. 2022, 144, 20067–20077. [DOI: 10.1021/jacs.2c09294] “Structure–Reactivity Relationships of Buchwald-Type Phosphines in Nickel-Catalyzed Cross-Couplings” Newman-Stonebraker, S. H.; Wang, J. Y.; Jeffrey P. D.; Doyle, A. G. J. Am. Chem. Soc. 2022, 144, 19635-19648. [DOI: 10.1021/jacs.2c09840] “Bioinspired Supercharging of Photoredox Catalysis for Applications in Energy and Chemical Manufacturing.” Millet, A.; Cesana, P. T.; Sedillo, K.; Bird, M. J.; Schlau-Cohen, G. S.; Doyle, A. G.; MacMillan, D. W. C.; Scholes, G. D. Acc. Chem. Res. 2022, 55, 1423-1434. [DOI: 10.1021/acs.accounts.2c00083] “Oxidative Addition of Aryl Halides to a Ni(I)-Bipyridine Complex.” Ting, S. I.; Williams, W. L.; Doyle, A. G. J. Am. Chem. Soc. 2022, 144, 5575-5582. [DOI: 10.1021/jacs.2c00462] “Auto-QChem: an automated workflow for the generation and storage of DFT calculations for organic molecules.” Żurański, A. M.; Wang, J. Y.; Shields, B. J.; Doyle, A. G. React. Chem. Eng. 2022, 7, 1276-1284. [DOI: 10.1039/D2RE00030J] “Using Data Science to Guide Aryl Bromide Substrate Scope Analysis in a Ni/Photoredox-Catalyzed Cross-Coupling with Acetals as Alcohol-Derived Radical Sources.” Kariofillis, S. K.; Jiang, S.; Żurański, A. M.; Gandhi, S. S.; Martinez Alvarado, J. I.; Doyle, A. G. J. Am. Chem. Soc. 2022, 144, 1045-1055. [DOI: 10.1021/jacs.1c12203] “A General Strategy for C(sp3)–H Functionalization with Nucleophiles Using Methyl Radical as a Hydrogen Atom Abstractor.” Leibler, I. N.-M.; Tekle-Smith, M. A.; Doyle, A. G. Nat. Commun. 2021, 12, 6950. [DOI: 10.1038/s41467-021-27165-z] “A Biohybrid Strategy for Enabling Photoredox Catalysis with Low-Energy Light.” 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. Chem. 2021, 8, 174-185. [DOI: 10.1016/j.chempr.2021.10.010] “The Open Reaction Database.” 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. J. Am. Chem. Soc. 2021, 143, 18820-18826. [DOI: 10.1021/jacs.1c09820] “The Evolution of Data-Driven Modeling in Organic Chemistry.” Williams, W. L.; Zeng, L.; Gensch, T.; Sigman, M. S.; Doyle, A. G.; Anslyn, E. V. ACS Cent. Sci. 2021, 7, 1622-1637. [10.1021/acscentsci.1c00535] “Phosphine/Photoredox Catalyzed Anti-Markovnikov Hydroamination of Olefins with Primary Sulfonamides via α-Scission from Phosphoranyl Radicals.” Chinn, A. J.; Sedillo, K; Doyle, A. G. J. Am. Chem. Soc 2021, 143, 18331-18338. [DOI: 10.1021/jacs.1c09484] “Univariate classification of phosphine ligation state and reactivity in cross-coupling catalysis.” Newman-Stonebraker, S. H.; Smith, S. R.; Borowski, J. E.; Peters, E.; Gensch, T.; Johnson, H. C.; Sigman, M. S.; Doyle, A. G. Science 2021, 374, 301-308. [DOI: 10.1126/science.ajb4213] “Ni/Photoredox-Catalyzed Enantioselective Cross-Electrophile Coupling of Styrene Oxides with Aryl Iodides.” Lau, S. H.; Borden, M. A.; Steiman, T. J.; Parasram, M.; Wang, L. S.; Doyle, A. G. J. Am. Chem. Soc 2021, 143, 15873-15881. [DOI: 10.1021/jacs.1c08105] “Predicting Reaction Yields via Supervised Learning.” Żurański, A. M.; Martinez Alvarado, J. I.; Shields, B. J.; Doyle, A. G. Acc. Chem. Res 2021, 54, 1856-1865. [DOI: 10.1021/acs.accounts.0c00770] “Automation and computer-assisted planning for chemical synthesis.” Shen, Y.; Borowski, J. E.; Hardy, M. A.; Sarpong, R.; Doyle, A. G.; Cernak, T. Nat. Rev. Methods Primers 2021, 1, 23. [DOI: 10.1038/s43586-021-00022-5] “Bayesian reaction optimization as a tool for chemical synthesis.” Shields, B. J.; Stevens, J.; Li, J.; Parasram, M.; Damani, F.; Martinez Alvarado, J. I.; Janey, J. M.; Adams, R. P.; Doyle, A. G. Nature 2021, 590, 89-96. [DOI: 10.1038/s41586-021-03213-y] “Synthetic and Mechanistic Implications of Chlorine Photoelimination in Nickel/Photoredox C(sp3)–H Cross-Coupling.” Kariofillis, S. K.; Doyle, A. G. Acc. Chem. Res. 2021, 54, 988-1000. [DOI: 10.1021/acs.accounts.0c00694] “Bioinspiration in Light Harvesting and Catalysis.” Proppe, A. H.; Li, Y. C.; Aspuru-Guzik, A.; Berlinguette, C. P.; Chang, C. J.; Cogdell, R.; Doyle, A. G.; Flick, J.; Gabor, N. M.; van Grondelle, R.; Hammes-Schiffer, S.; Jaffer, S. A.; Kelley, S. O.; Leclerc, M.; Leo, K.; Mallouk, T. E.; Narang, P.; Schlau-Cohen, G. S.; Scholes, G. D.; Vojvodic, A.; Yam, V. W.; Yang, J. Y.; Sargent, E. H. Nat. Rev. Mater. 2020, 5, 828-846. [DOI: 10.1038/s41578-020-0222-0] “Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis.” Webb, E. W.; Park, J. B.; Cole, E. L.; Donnelly, D. J.; Bonacorsi, S. J.; Ewing, W. R.; Doyle, A. G. J. Am. Chem. Soc. 2020, 142, 9493-9500. [DOI: 10.1021/jacs.0c03125] “Regioselective Cross-Electrophile Coupling of Epoxides and (Hetero)aryl Iodides via Ni/Ti/Photoredox Catalysis.” Parasram, M.; Shields, B. J.; Ahmad, O.; Knauber, T.; Doyle, A. G. ACS Catal 2020, 10, 5821-5827. [DOI: 10.1021/acscatal.0c01199] “Role of Electron-Deficient Olefin Ligands in a Ni-Catalyzed Aziridine Cross-Coupling To Generate Quaternary Carbons.” Estrada, J. G.; Williams, W. L.; Ting, S. I.; Doyle, A. G. J. Am. Chem. Soc. 2020, 142, 8928-8937. [DOI: 10.1021/jacs.0c02237] “Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source.” Kariofillis, S. K.; Shields, B. J.; Tekle-Smith, M. A.; Zacuto, M. J.; Doyle, A. G. J. Am. Chem. Soc. 2020, 142, 7683-7689. [DOI: 10.1021/jacs.0c02805] “Synthesis of β-Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides.” Steiman, T. J.; Liu, J.; Mengiste, A.; Doyle, A. G. J. Am. Chem. Soc. 2020, 142, 7598-7605. [DOI: 10.1021/jacs.0c01724] “3d-d Excited States of Ni(II) Complexes Relevant to Photoredox Catalysis: Spectroscopic Identification and Mechanistic Implications.” Ting, S. I.; Garakyaraghi, S.; Taliaferro, C. M.; Shields, B. J.; Scholes, G. D.; Castellano, F. N.; Doyle, A. G. J. Am. Chem. Soc. 2020, 142, 5800-5810. [DOI: 10.1021/jacs.0c00781] “Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes to Generate Dialkyl Ketones.” Martinez Alvarado, J. I.; Ertel, A. B.; Stegner, A.; Stache, E.; Doyle, A. G. Org. Lett. 2019, 21, 9940-9944. [DOI: 10.1021/acs.orglett.9b03871] “Discrete Object Generation with Reversible Inductive Construction.” Seff, A.; Zhou, W.; Damani, F.; Doyle, A. G.; Adams, R. P. [DOI: arXiv:1907.08268 [cs.LG]] “Response to Comment on ‘Predicting Reaction Performance in C-N Cross-Coupling Using Machine Learning.” Estrada, J. G.; Ahneman, D. T.; Sheridan, R. P.; Dreher, S. D.; Doyle, A. G. Science 2018, 362, 17402–17404. [10.1126/science.aat8763] “Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage-Independent Activation of Strong C-O Bonds.” Stache, E. E.; Ertel, A. B.; Rovis, T.; Doyle, A. G. ACS Catal. 2018, 8, 11134-11139. [DOI: 10.1021/acscatal.8b03592] “Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis.” Ackerman, L. K. G.; Martinez Alvarado, J. I.; Doyle, A. G. J. Am. Chem. Soc. 2018, 140, 14059-14063. [DOI: 10.1021/jacs.8b09191] “Deoxyfluorination with Sulfonyl Fluorides: Navigating Reaction Space with Machine Learning.” Nielsen, M. K.; Ahneman, D. T.; Riera, O.; Doyle, A. G. J. Am. Chem. Soc. 2018, 140, 5004-5008. [DOI: 10.1021/jacs.8b01523] “Predicting Reaction Performance in C-N Cross-Coupling Using Machine Learning.” Ahneman, D. T.; Estrada, J. G.; Lin, S.; Dreher, S. D.; Doyle, A. G. Science 2018, 360, 186-190. [DOI: 10.1126/science.aar5169] “Long-Lived Charge Transfer States of Nickel(II) Aryl Halide Complexes Facilitate Bimolecular Photoinduced Electron Transfer.” Shields, B. J.; Kudisch, B.; Scholes, G. D.; Doyle, A. G. J. Am. Chem. Soc. 2018, 140, 3035-3039. [DOI: 10.1021/jacs.7b13281] “Ni-Catalyzed Carbon-Carbon Bond-Forming Reductive Amination.” Heinz, C.; Lutz, J. P.; Simmons, E. M.; Miller, M. M.; Ewing, W. R.; Doyle, A. G. J. Am. Chem. Soc. 2018, 140, 2292-2300. [10.1021/jacs.0c03125] “Mild, Redox-Neutral Formylation of Aryl Chlorides via Photocatalytic Generation of Chlorine radicals.” Nielsen, M. K.; Shields, B. J.; Liu, J. Williams, M. J.; Zacuto, M. J; Doyle, A. G. Angew. Chem. Int. Ed. 2017, 56, 7191-7194. [DOI: 10.1002/ange.201702079] “Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines.” Woods, B. P.; Orlandi, M.; Huang, C.-Y. Sigman, M. H.; Doyle, A. G. J. Am. Chem. Soc. 2017, 139, 5688-5691. [DOI: 10.1021/jacs.7b03448] “Nickel-photoredox catalyzed enantioselective desymmetrization of meso cyclic anhydrides.” Angew. Chem. Int. Ed. 2017, 56, 3679-3683. [DOI:10.1002/anie.201700097] “Parameterization of phosphine ligands demonstrates enhancement of nickel catalysis via remote steric effects.” Wu, K.; Doyle, A. G. Nature Chem. 2017, 9, 779-784. [DOI:10.1038/nchem.2741] “Direct C(sp3)−H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals.” Shields, B. J.; Doyle, A. G. J. Am. Chem. Soc. 2016, 138, 12719−12722. [DOI: 10.1021/jacs.6b08397] “Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H–F Insertion.” Gray, E. E.; Nielsen, M. K.; Choquette, K. A.; Kalow, J. A.; Graham, T. J. A.; Doyle, A. G. J. Am. Chem. Soc. 2016, 138, 10802−10805. [DOI: 10.1021/jacs.6b06770] “C–H functionalization of amines with aryl halides by nickel-photoredox catalysis.” Ahneman, D. T.; Doyle, A. G. Chem. Sci. 2016, 7, 7002-7006. [DOI:10.1039/C6SC02815B] “Nickel-catalyzed enantioselective arylation of pyridine.” Lutz, J. P.; Chau, S. T.; Doyle, A. G. Chem. Sci. 2016, 7, 4105-4109. [DOI: 10.1039/C6SC00702C] “Direct Acylation of C(sp3)−H Bonds Enabled by Nickel and Photoredox Catalysis.” Joe, C. L.; Doyle, A. G. Angew. Chem. Int. Ed. 2016, 55, 4040-4043. [DOI: 10.1002/anie.201511438] “PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent.” Nielsen, M. K.; Ugaz, C. R.; Li, W.; Doyle, A. G. J. Am. Chem. Soc. 2015, 137, 9571−9574. [DOI: 10.1021/jacs.5b06307] “Dialkyl Ether Formation via Nickel-Catalyzed Cross Coupling of Acetals and Aryl Iodides.” Arendt, K. M.; Doyle, A. G. Angew. Chem. Int. Ed. 2015, 54, 9876-9880. [DOI: 10.1002/anie.201503936] “Electron-Deficient Olefin Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed Cross Coupling.” Huang, C.-Y.; Doyle, A. G. J. Am. Chem. Soc. 2015, 137, 5638−5641. [DOI: 10.1021/jacs.5b02503] “A Modular, Air-Stable Nickel Precatalyst.” Shields, J. D.; Gray, E. E.; Doyle, A. G. Org. Lett. 2015, 17, 2166−2169. [DOI: 10.1021/acs.orglett.5b00766]