Princeton Publications

55. 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 [10.1021/jacs.0c03125]

54. Parasram, M.; Shields, B. J.; Ahmad, O.; Knauber, T.; Doyle, A. G. “Regioselective Cross-Electrophile Coupling of Epoxides and (Hetero)aryl Iodides via Ni/Ti/Photoredox Catalysis” ACS Catal. 2020, 10, 5821-5827 [10.1021/acscatal.0c01199]

53. Estrada, J. G.; Williams, 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  [10.1021/jacs.0c02237]

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

51. 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 IodidesJ. Am. Chem. Soc. 2020142, 7598-7605 [10.1021/jacs.0c01724]

50. Ting, S. I.; Garakyaraghi, S.; Taliaferro, C. M.; Shields, B. J.; Scholes, G. D.; Castellano, F. N.; Doyle, A. G. ” 3d-d Excited States of Ni(II) Complexes Relevant to Photoredox Catalysis: Spectroscopic Identification and Mechanistic Implications” J. Am. Chem. Soc. 2020, 142, 5800-5810 [10.1021/jacs.0c00781]

49. Martinez Alvarado, J. I.; Ertel, A. B.; Stegner, A.; Stache, E.; Doyle, A. G. “Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes to Generate Dialkyl Ketones” Org. Lett. 2019, 21, 9940-9944 [10.1021/acs.orglett.9b03871]

48. Seff, A.; Zhou, W.; Damani, F.; Doyle, A. G.; Adams, R. P. “Discrete Object Generation with Reversible Inductive Construction” [arXiv:1907.08268 [cs.LG]]

47. Estrada, J. G.; Ahneman, D. T.; Sheridan, R. P.; Dreher, S. D.; Doyle, A. G. “Response to Comment on ‘Predicting Reaction Performance in C-N Cross-Coupling Using Machine Learning'” Science 2018, 362, eaat8763 [10.1126/science.aat8763]

46. Stache, E. E.; Ertel, A. B.; Rovis, T.; Doyle, A. G. “Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage-Independent Activation of Strong C-O Bonds” ACS Catal. 2018, 8, 11134-11139 [DOI: 10.1021/acscatal.8b03592]

45. 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. [DOI: 10.1021/jacs.8b09191]

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

43. 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. [DOI: 10.1126/science.aar5169]

42. Shields, B. J.; Kudisch, B.; Scholes, G. D.; Doyle, A. G. “Long-Lived Charge Transfer States of Nickel(II) Aryl Halide Complexes Facilitate Bimolecular Photoinduced Electron Transfer” J. Am. Chem. Soc. 2018, 140, 3035-3039. [DOI: 10.1021/jacs.7b13281]

41. 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. [DOI: 10.1021/jacs.7b12212]

40. Nielsen, M. K.; Shields, B. J.; Liu, J. Williams, M. J.; Zacuto, M. J; Doyle, A. G. “Mild, Redox-Neutral Formylation of Aryl Chlorides via Photocatalytic Generation of Chlorine radicals” Angew. Chem. Int. Ed. 201756, 7191-7194. [DOI: 10.1002/ange.201702079]

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

38. Stache, E. E.; Rovis, T.; Doyle, A. G. “Nickel-photoredox catalyzed enantioselective desymmetrization of meso cyclic anhydrides” Angew. Chem. Int. Ed. 201756, 3679-3683.  [DOI:10.1002/anie.201700097]

37. Wu, K.; Doyle, A. G. “Parameterization of phosphine ligands demonstrates enhancement of nickel catalysis via remote steric effects” Nature Chem. 2017, 9, 779-784. [DOI:10.1038/nchem.2741].  One of the most read articles in March and April.

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


35. Gray, E. E.; Nielsen, M. K.; Choquette, K. A.; Kalow, J. A.; Graham, T. J. A.; Doyle, A. G. “Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H–F Insertion” J. Am. ChemSoc. 2016, 138, 10802−10805. [DOI: 10.1021/jacs.6b06770].


34. Ahneman, D. T.; Doyle, A. G. “C–H functionalization of amines with aryl halides by nickel-photoredox catalysis” Chem. Sci. 2016, 7, 7002-7006. [DOI:10.1039/C6SC02815B].


33. Lutz, J. P.; Chau, S. T.; Doyle, A. G. “Nickel-catalyzed enantioselective arylation of pyridine” Chem. Sci. 2016, 7, 4105-4109. [DOI: 10.1039/C6SC00702C].

TOC Pyridinium

32. Joe, C. L.; Doyle, A. G. “Direct Acylation of C(sp3)−H Bonds Enabled by Nickel and Photoredox Catalysis” Angew. Chem. Int. Ed201655, 4040-4043. [DOI: 10.1002/anie.201511438].


31. Nielsen, M. K.; Ugaz, C. R.; Li, W.; Doyle, A. G. “PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent.” J. Am. ChemSoc. 2015, 137, 9571−9574. [DOI: 10.1021/jacs.5b06307Highlighted in Chem. & Eng. News and OPRD.

TOC graphic Revision 14jul2015

30. Arendt, K. M.; Doyle, A. G. “Dialkyl Ether Formation via Nickel-Catalyzed Cross Coupling of Acetals and Aryl Iodides.” Angew. Chem. Int. Ed201554, 9876-9880. [DOI: 10.1002/anie.201503936One of the most downloaded for the month of August.


29. Huang, C.-Y.; Doyle, A. G. “Electron-Deficient Olefin Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed Cross Coupling.” J. Am. ChemSoc. 2015, 137, 5638−5641. [DOI: 10.1021/jacs.5b02503One of the most downloaded papers in 2015.


28. Shields, J. D.; Gray, E. E.; Doyle, A. G. “A Modular, Air-Stable Nickel Precatalyst.” Org. Lett. 2015, 17,2166−2169. [DOI: 10.1021/acs.orglett.5b00766The most read article in April and May.


27. 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. [DOI: 10.1126/science.1255525Highlighted in Chem. & Eng. News. and Science Perspectives.

DTA, Science, 2014_TOC

26. Huang, C.-Y.; Doyle, A. G. “The Chemistry of Transition Metals with Three-Membered Ring Heterocycles.” Chem. Rev. 2014, 114, 8153-8198. [DOI: 10.1021/cr500036t]

CYH, ChemRev, 2014_TOC

25. 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. ChemSoc. 2014, 136, 5291-5294. [DOI: 10.1021/ja5025645Highlighted in SynfactsChem. & Eng. News.and Angewandte Highlights.


24. Katcher, M. H.; Norrby, P.-O.; Doyle, A. G. “Mechanistic Investigations of Palladium-Catalyzed Allylic Fluorination.” Organometallics. 2014, 33, 2121-2133. [DOI: 10.1021/om401240pOne of the most read papers between January-May. Featured on the issue’s cover

TOC MHK, Orgmet, 2014_TOC

23. Shields, J. D.; Ahneman, D. T.; Graham, T. J. A.; Doyle, A. G. “Enantioselective, Nickel-Catalyzed Suzuki Cross-Coupling of Quinolinium Ions.” Org. Lett. 2014, 16, 142-145. [DOI: 10.1021/ol4031364Highlighted in Synfacts.

JDS, OrgLett, 2013_TOC

22. Nielsen, D. K.; Huang, C.-Y.; Doyle, A. G. “Directed Nickel-Catalyzed Negishi Cross Coupling of Alkyl Aziridines.” J. Am. Chem. Soc. 2013, 135, 13605–13609. [DOI: 10.1021/ja407223g]

TOC graphic-5

21. Braun, M.-G.; Doyle, A. G. “Palladium-Catalyzed Allylic C–H Fluorination.” J. Am. Chem. Soc. 2013, 13512990–12993. [DOI: 10.1021/ja407223gHighlighted in Chem. & Eng. NewsOne of the most downloaded articles in August.


20. Chau, S. T.; Lutz, J. P.; Wu, K.; Doyle, A. G. “Nickel-Catalyzed Enantioselective Arylation of Pyridinium Ions: Harnessing an Iminium Ion Activation Mode.” Angew. Chem. Int. Ed. 2013, 52, 9153-9156. [DOI: 10.1002/anie.201303994Highlighted in Synfacts.

Chau, ACIE, 2013_TOC

19. Kalow, J. A.; Doyle, A. G. “Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis.” Tetrahedron 2013, 69, 5702-5709. [DOI: 10.1016/j.tet.2013.01.062] In honor of Professor Melanie Sanford on the occasion of her receipt of the Tetrahedron Young Investigator Award.  Highlighted in Synfacts.

JAK, Tetrahedron, 2013_TOC

18. Braun, M.-G.;‡ Katcher, M. H.;‡ Doyle, A. G. “Carbofluorination via a palladium-catalyzed cascade reaction.” Chem. Sci20134, 1216–1220.(‡ Equal contribution) [DOI: 10.1039/C2SC22198E] The most read article in January.  One of the most downloaded articles between January-March.

MGB, ChemSci, 2013_TOC

17. Sylvester, K. T.;‡ Wu, K.;‡ Doyle, A. G. “Mechanistic Investigation 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. (‡ Equal contribution) [DOI: 10.1021/ja3079362]

16. Kalow, J. A.; Schmitt, D. E.; Doyle, A. G. “Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines.” J. Org. Chem. 2012, 77, 4177–4183. [DOI: 10.1021/jo300433a] One of the most downloaded papers in April.

15. Huang, C.-Y.; Doyle, A. G. “Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines.” J. Am. Chem. Soc. 2012134, 9541–9544. [DOI: 10.1021/ja3013825] One of the most downloaded papers in March. Featured inJACS Spotlight and on the issue’s cover. Highlighted in Synfacts.


14. Graham, T. J. A.; Doyle, A. G. “Nickel-Catalyzed Cross-Coupling of Chromene Acetals and Boronic Acids.” Org. Lett. 201214, 1616–1619. [DOI: 10.1021/ol300364s] One of the most downloaded papers in March. Featured in OPRD.

TJG, OrgLett, 2012_TOC

13. 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. Synth. 201289, 9–18. [DOI: 10.15227/orgsyn.089.0009] Featured article on Org. Synth. homepage.

JAK, OrgSynth, 2012_TOC

12. Katcher, M. H.; Sha, A.; Doyle, A. G. “Palladium-Catalyzed Regio- and Enantioselective Fluorination of Acyclic Allylic Halides.” J. Am Chem. Soc. 2011133, 15902–15905. [DOI: 10.1021/ja206960k] One of the most downloaded articles in September. Highlighted in Synfacts.


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


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


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

TJG, ChemSci, 2011_TOC

8. Katcher, M. H.; Doyle, A. G. “Palladium-Catalyzed Asymmetric Synthesis of Allylic Fluorides.” J. Am. Chem. Soc2010132, 17402–17404. [DOI: 10.1021/ja109120n] Highlighted in OPRD. One of the most downloaded articles in November.


7. Kalow, J. A.; Doyle, A. G. “Enantioselective Ring Opening of Epoxides by Fluoride Anion Promoted by a Cooperative Dual Catalyst System.” J. Am. Chem. Soc2010132, 3268–3269. [DOI: 10.1021/ja100161d] Highlighted in SynfactsSynform, and OPRD. One of the most downloaded articles in February.


Prior Publications

6. Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. “Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions.” J. Am. Chem. Soc2008130, 7198–7199. [DOI: 10.1021/ja801514m]

5. Doyle, A. G.; Jacobsen, E. N. “Small-Molecule H-Bond Donors in Asymmetric Catalysis.” Chem. Rev2007107, 5713–5743. [DOI: 10.1021/cr068373r]

4. Doyle, A. G.; Jacobsen, E. N. “Enantioselective Alkylation of Acyclic α,α-Disubstituted Tributyltin Enolates Catalyzed by a Cr(salen) Complex.” Angew. Chem. Int. Ed2007, 46, 3701–3705. [DOI: 10.1002/anie.200604901]

3. Doyle, A. G.; Jacobsen, E. N. “Enantioselective Alkylations of Tributyltin Enolates Catalyzed by Cr(salen)Cl: Access to Enantiomerically Enriched All-Carbon Quaternary Centers.” J. Am. Chem. Soc2005127, 62–63. [DOI: 10.1021/ja043601p]

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

1. White, M. C.; Doyle, A. G.; Jacobsen, E. N. “A Synthetically Useful, Self-Assembling MMO Mimic System for Catalytic Alkene Epoxidation with Aqueous H2O2.” J. Am. Chem. Soc2001123, 7194–7195. [DOI: 10.1021/ja015884g] Highlighted in Chem. & Eng. News.