2022

71. “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. [10.1021/acs.accounts.2c00083] Link PDF

70. “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. [10.1021/jacs.2c00462] Link PDF

69. “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. [10.1039/D2RE00030J] Link PDF

68. “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. [10.1021/jacs.1c12203] Link PDF

2021

67. “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. [10.1038/s41467-021-27165-z] Link PDF

66. “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. [10.1016/j.chempr.2021.10.010] Link PDF

65. “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. [10.1021/jacs.1c09820] Link PDF

64. “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. [10.1021/acscentsci.1c00535] Link PDF

63. “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. [10.1021/jacs.1c09484] Link PDF

62. 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. [10.1126/science.ajb4213] Link PDF

61. 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.  [10.1021/jacs.1c08105] Link PDF

60. 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. [10.1021/acs.accounts.0c00770] Link PDF

59. “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 20211, 23. [10.1038/s43586-021-00022-5] Link PDF

58. “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 2021590, 89-96. [10.1038/s41586-021-03213-y] Github

57. 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. [10.1021/acs.accounts.0c00694] Link PDF

2020

56. “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. [10.1038/s41578-020-0222-0] Link PDF

55. “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. 2020142, 9493-9500. [10.1021/jacs.0c03125] Link PDF

54. “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 202010, 5821-5827. [10.1021/acscatal.0c01199] Link PDF

53. “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. 2020142, 8928-8937. [10.1021/jacs.0c02237] Link PDF

52. “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. 2020142, 7683-7689. [10.1021/jacs.0c02805] Link PDF

51. “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. 2020142, 7598-7605. [10.1021/jacs.0c01724] Link PDF

50. “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. 2020142, 5800-5810. [10.1021/jacs.0c00781] Link PDF

2019

49. “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. 201921, 9940-9944. [DOI: 10.1021/acs.orglett.9b03871] Link PDF

2018

48. “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]]Link PDF

47. “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 2018362, 17402–17404. [10.1126/science.aat8763] Link PDF Github

46. “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. 20188, 11134-11139. [DOI: 10.1021/acscatal.8b03592] Link PDF

45. “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. 2018140, 14059-14063. [DOI: 10.1021/jacs.8b09191] Link PDF

44. “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. 2018140, 5004-5008. [DOI: 10.1021/jacs.8b01523] Link PDF

43. “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  2018360, 186-190. [DOI: 10.1126/science.aar5169] Link PDF

42. “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. 2018140, 3035-3039. [DOI: 10.1021/jacs.7b13281] Link PDF

41. “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. 2018140, 2292-2300. [10.1021/jacs.0c03125] Link PDF

2017

40. “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. 201756, 7191-7194. [DOI: 10.1002/ange.201702079] Link PDF

39. “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. 2017139, 5688-5691. [DOI: 10.1021/jacs.7b03448] Link PDF

38. “Nickel-photoredox catalyzed enantioselective desymmetrization of meso cyclic anhydrides.” Angew. Chem. Int. Ed. 201756, 3679-3683. [DOI:10.1002/anie.201700097] Link PDF

37. “Parameterization of phosphine ligands demonstrates enhancement of nickel catalysis via remote steric effects.” Wu, K.; Doyle, A. G. Nature Chem. 20179, 779-784. [DOI:10.1038/nchem.2741] Link PDF

2016

36. “Direct C(sp3)−H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals.” Shields, B. J.; Doyle, A. G. J. Am. Chem. Soc. 2016138, 12719−12722. [DOI: 10.1021/jacs.6b08397] Link PDF

35. “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. 2016138, 10802−10805. [DOI: 10.1021/jacs.6b06770] Link PDF

34. “C–H functionalization of amines with aryl halides by nickel-photoredox catalysis.” Ahneman, D. T.; Doyle, A. G.  Chem. Sci.  20167, 7002-7006. [DOI:10.1039/C6SC02815B] Link PDF

33. “Nickel-catalyzed enantioselective arylation of pyridine.” Lutz, J. P.; Chau, S. T.; Doyle, A. G. Chem. Sci. 20167, 4105-4109. [DOI: 10.1039/C6SC00702C] Link PDF

32. “Direct Acylation of C(sp3)−H Bonds Enabled by Nickel and Photoredox Catalysis.” Joe, C. L.; Doyle, A. G. Angew. Chem. Int. Ed. 201655, 4040-4043. [DOI: 10.1002/anie.201511438] Link PDF

2015

31. “PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent.” Nielsen, M. K.; Ugaz, C. R.; Li, W.; Doyle, A. G. J. Am. Chem. Soc. 2015137, 9571−9574. [DOI: 10.1021/jacs.5b06307]Link PDF

30. “Dialkyl Ether Formation via Nickel-Catalyzed Cross Coupling of Acetals and Aryl Iodides.” Arendt, K. M.; Doyle, A. G. Angew. Chem. Int. Ed. 201554, 9876-9880. [DOI: 10.1002/anie.201503936]Link PDF

29. “Electron-Deficient Olefin Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed Cross Coupling.” Huang, C.-Y.; Doyle, A. G. J. Am. Chem. Soc. 2015137, 5638−5641. [DOI: 10.1021/jacs.5b02503]Link PDF

28. “A Modular, Air-Stable Nickel Precatalyst.” Shields, J. D.; Gray, E. E.; Doyle, A. G. Org. Lett. 201517, 2166−2169. [DOI: 10.1021/acs.orglett.5b00766]Link PDF

2014

27. “Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp3-carbons with aryl halides.” Zuo, Z.; Ahneman, D.; Chu, L.; Terrett, J.; Doyle, A. G.; MacMillan, D. W. C.  Science  2014345, 437-440. [DOI: 10.1126/science.1255525]Link PDF

26. “The Chemistry of Transition Metals with Three-Membered Ring Heterocycles.” Huang, C.-Y.; Doyle, A. G. Chem. Rev. 2014114, 8153-8198. [DOI: 10.1021/cr500036t]Link PDF

25. “Enantioselective radiosynthesis of positron emission tomography (PET) tracers containing [18F]fluorohydrins.” Graham, T. J. A.; Lambert, R. F.; Ploessl, K.; Kung, H. F.; Doyle, A. G. J. Am. Chem. Soc. 2014136, 5291-5294. [DOI: 10.1021/ja5025645]Link PDF

24. “Mechanistic Investigations of Palladium-Catalyzed Allylic Fluorination.” Katcher, M. H.; Norrby, P.-O.; Doyle, A. G.  Organometallics. 201433, 2121-2133. [DOI: 10.1021/om401240p]Link PDF

23. “Enantioselective, Nickel-Catalyzed Suzuki Cross-Coupling of Quinolinium Ions.” Shields, J. D.; Ahneman, D. T.; Graham, T. J. A.; Doyle, A. G. Org. Lett. 201416, 142-145. [DOI: 10.1021/ol4031364]Link PDF

2013

22. “Directed Nickel-Catalyzed Negishi Cross Coupling of Alkyl Aziridines.” Nielsen, D. K.; Huang, C.-Y.; Doyle, A. G.  J. Am. Chem. Soc. 2013135, 13605–13609. [DOI: 10.1021/ja407223g]Link PDF

21. “Palladium-Catalyzed Allylic C–H Fluorination.” Braun, M.-G.; Doyle, A. G. J. Am. Chem. Soc. 2013135, 12990–12993. [DOI: 10.1021/ja407223g]Link PDF

20. “Nickel-Catalyzed Enantioselective Arylation of Pyridinium Ions: Harnessing an Iminium Ion Activation Mode.” Chau, S. T.; Lutz, J. P.; Wu, K.; Doyle, A. G. Angew. Chem. Int. Ed. 201352, 9153-9156. [DOI: 10.1002/anie.201303994]Link PDF

19. “Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis.” Kalow, J. A.; Doyle, A. G.  Tetrahedron  201369, 5702-5709. [DOI: 10.1016/j.tet.2013.01.062]Link PDF

18. “Carbofluorination via a palladium-catalyzed cascade reaction.” Braun, M.-G.;‡ Katcher, M. H.;‡ Doyle, A. G. Chem. Sci.  20134, 1216–1220. (‡ Equal contribution) [DOI: 10.1039/C2SC22198E]Link PDF

2012

17. “Mechanistic Investigation of the Nickel-Catalyzed Suzuki Reaction of N,O-Acetals: Evidence for Boronic Acid-Assisted Oxidative Addition and an Iminium Activation Pathway.” Sylvester, K. T.;‡ Wu, K.;‡ Doyle, A. G. J. Am. Chem. Soc. 2012134, 16967-16970. (‡ Equal contribution) [DOI: 10.1021/ja3079362]Link PDF

16. “Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines.” Kalow, J. A.; Schmitt, D. E.; Doyle, A. G. Org. Chem. 201277, 4177–4183. [DOI: 10.1021/jo300433a]Link PDF

15. “Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines.” Huang, C.-Y.; Doyle, A. G. J. Am. Chem. Soc. 2012134, 9541–9544. [DOI: 10.1021/ja3013825] Link PDF

14. “Nickel-Catalyzed Cross-Coupling of Chromene Acetals and Boronic Acids.” Graham, T. J. A.; Doyle, A. G. Org. Lett. 201214, 1616–1619. [DOI: 10.1021/ol300364s]Link PDF

13. “Fluoride Ring-Opening Kinetic Resolution of Terminal Epoxides: Preparation of (S)-2-Fluoro-1-Phenylethanol.” Shaw, T. W.; Kalow, J. A.; Doyle, A. G. Org. Synth. 201289, 9–18. [DOI: 10.15227/orgsyn.089.0009]Link PDF

2011

12. “Palladium-Catalyzed Regio- and Enantioselective Fluorination of Acyclic Allylic Halides.” Katcher, M. H.; Sha, A.; Doyle, A. G. J. Am. Chem. Soc. 2011133, 15902–15905. [DOI: 10.1021/ja206960k] Link PDF

11. “Mechanistic Investigations of Cooperative Catalysis in the Enantioselective Fluorination of Epoxides.” Kalow, J. A.; Doyle, A. G. J. Am. Chem. Soc. 2011133, 16001–16012. [DOI: 10.1021/ja207256s] Link PDF

10. “Nickel-Catalyzed Cross Coupling of Styrenyl Epoxides with Boronic Acids.” Nielsen, D. K.; Doyle, A. G. Angew. Chem., Int. Ed. 201150, 6056–6059. [DOI: 10.1002/anie.201101191] Link PDF

9. “Transition Metal-Catalyzed Cross Coupling with N-Acyliminium Ions Derived from Quinolines and Isoquinolines.” Graham, T. J. A.; Shields, J. D.; Doyle, A. G.Chem. Sci. 20112, 980–984. [DOI: 10.1039/c1sc00026h] Link PDF

2010

8. “Palladium-Catalyzed Asymmetric Synthesis of Allylic Fluorides.” Katcher, M. H.; Doyle, A. G. J. Am. Chem. Soc. 2010132, 17402–17404. [DOI: 10.1021/jacs.0c03125] Link PDF

7. “Enantioselective Ring Opening of Epoxides by Fluoride Anion Promoted by a Cooperative Dual Catalyst System.” Kalow, J. A.; Doyle, A. G. J. Am. Chem. Soc. 2010132, 3268–3269. [DOI: 10.1021/ja100161d] Link PDF

Prior Publications

6. “Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions.” Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008130, 7198–7199. [DOI: 10.1021/ja801514m] Link PDF

5. “Small-Molecule H-Bond Donors in Asymmetric Catalysis.” Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007107, 5713–5743. [DOI: 10.1021/cr068373r] Link PDF

4. “Enantioselective Alkylation of Acyclic α,α-Disubstituted Tributyltin Enolates Catalyzed by a Cr(salen) Complex.” Doyle, A. G.; Jacobsen, E. N. Angew. Chem. Int. Ed. 200746, 3701–3705. [DOI: 10.1002/anie.200604901] Link PDF

3. “Enantioselective Alkylations of Tributyltin Enolates Catalyzed by Cr(salen)Cl: Access to Enantiomerically Enriched All-Carbon Quaternary Centers.” Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2005127, 62–63. [DOI: 10.1021/ja043601p] Link PDF

2.C-Arylglucoside synthesis: triisopropylsilane as a selective reagent for the reduction of an anomeric C-phenyl ketal.” Ellsworth, B. A.; Doyle, A. G.; Patel, M.; Caceres-Cortes, J.; Meng, W.; Deshpande, P. P.; Pullockaran, A.; Washburn, W. N. Tetrahedron: Asymmetry 200314, 3243–3247 [DOI: 10.1016/j.tetasy.2003.08.007] Link PDF

1.“A Synthetically Useful, Self-Assembling MMO Mimic System for Catalytic Alkene Epoxidation with Aqueous H2O2.” White, M. C.; Doyle, A. G.; Jacobsen, E. N.  J. Am. Chem. Soc. 2001123, 7194–7195 [DOI: 10.1021/ja015884g] Link PDF