Publications-Sorted2020-09-11T14:10:31-07:00

Publications

93. Multi-Threshold Analysis for Chemical Space Mapping of Ni-Catalyzed Suzuki-Miyaura Couplings2024-10-25T21:41:13-07:00

“Multi-Threshold Analysis for Chemical Space Mapping of Ni-Catalyzed Suzuki-Miyaura Couplings” LeSueur, A.; Tao, N.; Doyle, A. G.; Sigman, M. Eur. J. Org. Chem., 2024, e202400428. [DOI: 10.1002/ejoc.202400428] Link PDF

 

92. Cooperative Phosphine-Photoredox Catalysis Enables N–H Activation of Azoles for Intermolecular Olefin Hydroamination2024-08-06T13:50:52-07:00

“Cooperative Phosphine-Photoredox Catalysis Enables N–H Activation of Azoles for Intermolecular Olefin Hydroamination” Sedillo, K.; Fan, F.; Knowles, R. R.; Doyle, A. G. J. Am. Chem. Soc., 2024, 146, 20349-20356. [DOI: 10.1021/jacs.4c05881] Link PDF

 

91. Mechanism of Ni-Catalyzed Photochemical Halogen Atom-Mediated C(sp3)–H Arylation2024-07-10T12:37:22-07:00

“Mechanism of Ni-Catalyzed Photochemical Halogen Atom-Mediated C(sp3)–H Arylation” Cusumano, A. Q; Chaffin, B. C.; Doyle, A. G. J. Am. Chem. Soc., 2024, 146, 15331-15344. [DOI: 10.1021/jacs.4c03099] Link PDF

 

90. Autonomous closed-loop mechanistic investigation of molecular electrochemistry via automation2024-05-27T18:36:11-07:00

“Autonomous closed-loop mechanistic investigation of molecular electrochemistry via automation” 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. Nat. Commun, 2024, 15, 2781. [DOI: 10.1038/s41467-024-47210-x] Link PDF

89. Data Science Guided Multiobjective Optimization of a Stereoconvergent Nickel-Catalyzed Reduction of Enol Tosylates to Access Trisubstituted Alkenes2024-05-27T18:33:20-07:00

“Data Science Guided Multiobjective Optimization of a Stereoconvergent Nickel-Catalyzed Reduction of Enol Tosylates to Access Trisubstituted Alkenes” 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. ACS Catal, 2024, 14, 4699-4708. [DOI: 10.1021/acscatal.4c00650] Link PDF

88. Identifying general reaction conditions by bandit optimization2024-05-27T18:33:07-07:00

“Identifying general reaction conditions by bandit optimization” 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. Nature, 2024, 626, 1025-1033. [DOI: 10.1038/s41586-024-07021-y] Link PDF

87. Broad Survey of Selectivity in the Heterogeneous Hydrogenation of Heterocycles2024-05-27T18:32:51-07:00

“Broad Survey of Selectivity in the Heterogeneous Hydrogenation of Heterocycles” Lyons, T. W.; Leibler, I. N.-M.; He, C. Q.; Gadamsetty, S.; Estrada, G. J.; Doyle, A. G. J. Org. Chem. 2024, 89, 1438-1445.
[DOI: 10.1021/acs.joc.3c02028] Link PDF

86. Catalyst Deactivation of a Monoligated CyJohnPhos-Bound Nickel(0) Complex2024-05-27T18:32:36-07:00

“Catalyst Deactivation of a Monoligated CyJohnPhos-Bound Nickel(0) Complex” Newman-Stonebraker, S. H.; Raab, T. J.; Doyle, A. G. Organometallics 2023, 42, 3438-3441.
[DOI: 10.1021/jacs.3c08301] Link PDF

85. Dataset Design for Building Models of Chemical Reactivity2024-05-27T18:32:22-07:00

“Dataset Design for Building Models of Chemical Reactivity” Raghavan, P; Haas, B. C.; Ruos, M. E.; Schleinitz, J; Doyle, A. G.; Reisman, S. E.; Sigman, M. S.; Coley, C. W. J. Am. Chem. Soc. 2023, 145, 24175-24183.
[DOI: 10.1021/jacs.3c08301] Link PDF

84. Branched-Selective Cross-Electrophile Coupling of 2-Alkyl Aziridines and (Hetero)aryl Iodides Using Ti/Ni Catalysis2024-05-27T18:32:07-07:00

“Branched-Selective Cross-Electrophile Coupling of 2-Alkyl Aziridines and (Hetero)aryl Iodides Using Ti/Ni Catalysis” Williams, W. L.; Gutiérrez-Valencia, N. E.; Doyle, A. G. J. Am. Chem. Soc. 2023, 145, 24175-24183.
[DOI: 10.1021/jacs.3c08301] Link PDF

83. Synthesis of Nickel(I)–Bromide Complexes via Oxidation and Ligand Displacement: Evaluation of Ligand Effects on Speciation and Reactivity2024-05-27T18:31:51-07:00

“Synthesis of Nickel(I)–Bromide Complexes via Oxidation and Ligand Displacement: Evaluation of Ligand Effects on Speciation and Reactivity” Newman-Stonebraker, S. H.; Raab, T. J.; Roshandel, H. R.; Doyle, A. G. J. Am. Chem. Soc. 2023, 145, 19368-19377.
[DOI: 10.1021/jacs.3c06233] Link PDF

82. A General Photocatalytic Strategy for Nucleophilic Amination of Primary and Secondary Benzylic C–H Bonds2024-05-27T18:31:32-07:00

“A General Photocatalytic Strategy for Nucleophilic Amination of Primary and Secondary Benzylic C–H Bonds” Ruos, M. E.; Kinney, R. G.; Ring, O. T.; Doyle, A. G. J. Am. Chem. Soc. 2023, 145, 18487-18496.
[DOI: 10.1021/jacs.3c04912] Link PDF

81. Continuous flow synthesis of pyridinium salts accelerated by multi-objective Bayesian optimization with active learning2024-05-27T18:31:12-07:00

“Continuous flow synthesis of pyridinium salts accelerated by multi-objective Bayesian optimization with active learning” 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. Chem. Sci. 2023, 14, 8061-8069.
[DOI: 10.1039/d3sc01303k] Link PDF

80. Comparison of Monophosphine and Bisphosphine Precatalysts for Ni-Catalyzed Suzuki–Miyaura Cross-Coupling: Understanding the Role of the Ligation State in Catalysis2023-06-05T13:39:19-07:00

Borowski, J. E.; Newman-Stonebraker, S. H.; Doyle, A. G. ACS. Catal. 2023, 13, 7966-7977.
[DOI: 10.1021/acscatal.3c01331] Link PDF

79. Strategies for Nucleophilic C(sp3)–(Radio)Fluorination2023-05-31T15:56:07-07:00

Leibler, I. N.-M.; Gandhi, S. S.; Tekle-Smith, M. A.; Doyle, A. G. J. Am. Chem. Soc. 2023, 145, 9928-9950.
[DOI: 10.1021/jacs.3c01824] Link PDF

78. Interrogating the Mechanistic Features of Ni(I)-Mediated Aryl Iodide Oxidative Addition Using Electroanalytical and Statistical Modeling Techniques2023-04-25T09:16:29-07:00

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] Link PDF

77. A Machine Learning Approach to Model Interaction Effects: Development and Application to Alcohol Deoxyfluorination2023-04-13T09:16:02-07:00

Żurański, A. M.; Gandhi, S. S.; Doyle, A. G. J. Am. Chem. Soc. 2023, 145, 7898–7909.
[DOI: 10.1021/jacs.2c13093] Link PDF

76. On the Use of Real-World Datasets for Reaction Yield Prediction2023-03-29T12:37:42-07:00

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] Link PDF

 

75. Radical Redox Annulations: A General Light-Driven Method for the Synthesis of Saturated Heterocycles2022-12-30T17:39:02-08:00

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] Link PDF

74. A Multi-Objective Active Learning Platform and Web App for Reaction Optimization2022-12-30T17:36:45-08:00

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] Link PDF Link EDBO+ web app.

73. Ni/Photoredox-Catalyzed C(sp3)–C(sp3) Coupling between Aziridines and Acetals as Alcohol-Derived Alkyl Radical Precursors2022-12-30T17:42:21-08:00

Dongbang, S; Doyle, A. G. J. Am. Chem. Soc. 2022, 144, 20067–20077.
[DOI: 10.1021/jacs.2c09294] Link PDF

72. Structure–Reactivity Relationships of Buchwald-Type Phosphines in Nickel-Catalyzed Cross-Couplings2022-12-30T17:30:50-08:00

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] Link PDF

71. Bioinspired Supercharging of Photoredox Catalysis for Applications in Energy and Chemical Manufacturing2022-12-30T17:27:44-08:00

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] Link PDF

70. Oxidative Addition of Aryl Halides to a Ni(I)-Bipyridine Complex2022-12-30T17:15:24-08:00

Ting, S. I.; Williams, W. L.; Doyle, A. G. J. Am. Chem. Soc. 2022, 144, 5575-5582.
[DOI: 10.1021/jacs.2c00462] Link PDF

69. Auto-QChem: an automated workflow for the generation and storage of DFT calculations for organic molecules2022-12-30T17:12:18-08:00

Żurański, A. M.; Wang, J. Y.; Shields, B. J.; Doyle, A. G. React. Chem. Eng. 2022, 7, 1276-1284.
[DOI: 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 Sources2022-12-30T17:04:00-08:00

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] Link PDF

67. A General Strategy for C(sp3)–H Functionalization with Nucleophiles Using Methyl Radical as a Hydrogen Atom Abstractor2022-12-30T17:01:58-08:00

Leibler, I. N.-M.; Tekle-Smith, M. A.; Doyle, A. G. Nat. Commun. 2021, 12, 6950.
[DOI: 10.1038/s41467-021-27165-z] Link PDF

66. A Biohybrid Strategy for Enabling Photoredox Catalysis with Low-Energy Light2022-12-30T20:32:18-08:00

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] Link PDF

65. The Open Reaction Database2022-12-30T20:29:25-08:00

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] Link PDF

64. The Evolution of Data-Driven Modeling in Organic Chemistry2022-12-30T20:30:20-08:00

Williams, W. L.; Zeng, L.; Gensch, T.; Sigman, M. S.; Doyle, A. G.; Anslyn, E. V. ACS Cent. Sci. 2021, 7, 1622-1637.
[DOI: 10.1021/acscentsci.1c00535] Link PDF

63. Phosphine/Photoredox Catalyzed Anti-Markovnikov Hydroamination of Olefins with Primary Sulfonamides via α-Scission from Phosphoranyl Radicals2022-12-30T20:30:50-08:00

Chinn, A. J.; Sedillo, K.; Doyle, A. G.  J. Am. Chem. Soc. 2021, 143, 18331-18338.
[DOI: 10.1021/jacs.1c09484] Link PDF

62. Univariate classification of phosphine ligation state and reactivity in cross-coupling catalysis2022-12-30T16:48:28-08:00

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] Link PDF

61. Ni/Photoredox-Catalyzed Enantioselective Cross-Electrophile Coupling of Styrene Oxides with Aryl Iodides2022-12-30T16:44:26-08:00

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] Link PDF

60. Predicting Reaction Yields via Supervised Learning2022-12-30T20:33:10-08:00

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] Link PDF

59. Automation and computer-assisted planning for chemical synthesis2022-12-30T20:33:39-08:00

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] Link PDF

58. Bayesian reaction optimization as a tool for chemical synthesis2022-12-30T16:28:13-08:00

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] Link PDF

57. Synthetic and Mechanistic Implications of Chlorine Photoelimination in Nickel/Photoredox C(sp3)–H Cross-Coupling2022-12-30T20:34:14-08:00

Kariofillis, S. K.; Doyle, A. G. Acc. Chem. Res. 2021, 54, 988-1000.
[DOI: 10.1021/acs.accounts.0c00694] Link PDF

56. Bioinspiration in Light Harvesting and Catalysis2022-12-30T20:35:01-08:00

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] Link PDF

55. Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis2022-12-30T16:18:13-08:00

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] Link PDF

Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis

54. Regioselective Cross-Electrophile Coupling of Epoxides and (Hetero)aryl Iodides via Ni/Ti/Photoredox Catalysis2022-12-30T16:17:21-08:00

Parasram, M.; Shields, B. J.; Ahmad, O.; Knauber, T.; Doyle, A. G.  ACS Catal. 2020, 10, 5821-5827.
[DOI: 10.1021/acscatal.0c01199] Link PDF

Regioselective Cross-Electrophile Coupling of Epoxides and (Hetero)aryl Iodides via Ni/Ti/Photoredox Catalysis

53. Role of Electron-Deficient Olefin Ligands in a Ni-Catalyzed Aziridine Cross-Coupling To Generate Quaternary Carbons2022-12-30T16:14:27-08:00

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] Link PDF

Role of Electron-Deficient Olefin Ligands in a Ni-Catalyzed Aziridine Cross-Coupling To Generate Quaternary Carbons

52. Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source2022-12-30T16:13:51-08:00

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] Link PDF

Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source

51. Synthesis of β-Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides2022-12-30T16:13:22-08:00

Steiman, T. J.; Liu, J.; Mengiste, A.; Doyle, A. G. J. Am. Chem. Soc. 2020, 142, 7598-7605.
[DOI: 10.1021/jacs.0c01724] Link PDF

Synthesis of β-Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides

50. 3d-d Excited States of Ni(II) Complexes Relevant to Photoredox Catalysis: Spectroscopic Identification and Mechanistic Implications2022-12-30T16:12:00-08:00

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] Link PDF

3d-d Excited States of Ni(II) Complexes Relevant to Photoredox Catalysis: Spectroscopic Identification and Mechanistic Implications

49. Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes to Generate Dialkyl Ketones2022-12-30T16:11:21-08:00

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] Link PDF

Direct Use of Carboxylic Acids in the Photocatalytic Hydroacylation of Styrenes to Generate Dialkyl Ketones

48. Discrete Object Generation with Reversible Inductive Construction2022-12-30T16:07:20-08:00

Seff, A.; Zhou, W.; Damani, F.; Doyle, A. G.; Adams, R. P.
[arXiv:1907.08268 [cs.LG]] Link PDF

47. Response to Comment on ‘Predicting Reaction Performance in C-N Cross-Coupling Using Machine Learning2022-12-30T16:30:25-08:00

Estrada, J. G.; Ahneman, D. T.; Sheridan, R. P.; Dreher, S. D.; Doyle, A. G. Science 2018, 362, eaat8763
[DOI: 10.1126/science.aat8763] Link PDF

Response to Comment on ‘Predicting Reaction Performance in C-N Cross-Coupling Using Machine Learning

46. Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage-Independent Activation of Strong C-O Bonds2022-12-30T16:01:28-08:00

Stache, E. E.; Ertel, A. B.; Rovis, T.; Doyle, A. G. ACS Catal. 2018, 8, 11134-11139.
[DOI: 10.1021/acscatal.8b03592] Link PDF

Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage-Independent Activation of Strong C-O Bonds

45. Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis2022-12-30T16:00:58-08:00

Ackerman, L. K. G.; Martinez Alvarado, J. I.; Doyle, A. G.  J. Am. Chem. Soc. 2018, 140, 14059-14063.
[DOI: 10.1021/jacs.8b09191] Link PDF

Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis

44. Deoxyfluorination with Sulfonyl Fluorides: Navigating Reaction Space with Machine Learning2022-12-30T16:00:14-08:00

Nielsen, M. K.; Ahneman, D. T.; Riera, O.; Doyle, A. G.  J. Am. Chem. Soc. 2018, 140, 5004-5008.
[DOI: 10.1021/jacs.8b01523] Link PDF

Deoxyfluorination with Sulfonyl Fluorides: Navigating Reaction Space with Machine Learning

43. Predicting Reaction Performance in C-N Cross-Coupling Using Machine Learning2022-12-30T16:31:17-08:00

Ahneman, D. T.; Estrada, J. G.; Lin, S.; Dreher, S. D.; Doyle, A. G. Science 2018, 360, 186-190.
[DOI: 10.1126/science.aar5169] Link PDF

Predicting Reaction Performance in C-N Cross-Coupling Using Machine Learning

42. Long-Lived Charge Transfer States of Nickel(II) Aryl Halide Complexes Facilitate Bimolecular Photoinduced Electron Transfer2022-12-30T15:57:11-08:00

Shields, B. J.; Kudisch, B.; Scholes, G. D.; Doyle, A. G. J. Am. Chem. Soc. 2018, 140, 3035-3039.
[DOI: 10.1021/jacs.7b13281] Link PDF

Long-Lived Charge Transfer States of Nickel(II) Aryl Halide Complexes Facilitate Bimolecular Photoinduced Electron Transfer

41. Ni-Catalyzed Carbon-Carbon Bond-Forming Reductive Amination2020-09-22T00:49:22-07:00

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.
[DOI: 10.1021/jacs.7b12212] Link PDF

Ni-Catalyzed Carbon-Carbon Bond-Forming Reductive Amination

40. Mild, Redox-Neutral Formylation of Aryl Chlorides via Photocatalytic Generation of Chlorine radicals2020-09-22T00:49:28-07:00

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] Link PDF

Mild, Redox-Neutral Formylation of Aryl Chlorides via Photocatalytic Generation of Chlorine radicals

39. Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines2020-09-22T00:50:00-07:00

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] Link PDF

Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines

38. Nickel-photoredox catalyzed enantioselective desymmetrization of meso cyclic anhydrides2020-09-22T00:50:03-07:00

Angew. Chem. Int. Ed. J. Am. Chem. Soc. 2017, 56, 3679-3683.
[DOI:10.1002/anie.201700097] Link PDF

Nickel-photoredox catalyzed enantioselective desymmetrization of meso cyclic anhydrides

37. Parameterization of phosphine ligands demonstrates enhancement of nickel catalysis via remote steric effects2020-09-22T00:50:08-07:00

Wu, K.; Doyle, A. G. Nature Chem. 2017, 9, 779-784.
[DOI:10.1038/nchem.2741] Link PDF

Parameterization of phosphine ligands demonstrates enhancement of nickel catalysis via remote steric effects

36. Direct C(sp3)−H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals2020-09-22T00:50:12-07:00

Shields, B. J.; Doyle, A. G. J. Am. Chem. Soc. 2016, 138, 12719−12722.
[DOI: 10.1021/jacs.6b08397] Link PDF

Direct C(sp3)−H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals

35. Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H–F Insertion2020-09-22T00:50:17-07:00

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] Link PDF

Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H–F Insertion

34. C–H functionalization of amines with aryl halides by nickel-photoredox catalysis2022-12-30T15:52:25-08:00

Ahneman, D. T.; Doyle, A. G.  Chem. Sci. 2016, 7, 7002-7006.
[DOI:10.1039/C6SC02815B] Link PDF

C–H functionalization of amines with aryl halides by nickel-photoredox catalysis

33. Nickel-catalyzed enantioselective arylation of pyridine2020-09-22T00:50:28-07:00

Lutz, J. P.; Chau, S. T.; Doyle, A. G. Chem. Sci. 2016, 7, 4105-4109.
[DOI: 10.1039/C6SC00702C] Link PDF

Nickel-catalyzed enantioselective arylation of pyridine

32. Direct Acylation of C(sp3)−H Bonds Enabled by Nickel and Photoredox Catalysis2020-09-22T00:50:34-07:00

Joe, C. L.; Doyle, A. G. Angew. Chem. Int. Ed. 2016, 55, 4040-4043.
[DOI: 10.1002/anie.201511438] Link PDF

Direct Acylation of C(sp3)−H Bonds Enabled by Nickel and Photoredox Catalysis

31. PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent2020-09-22T00:50:38-07:00

Nielsen, M. K.; Ugaz, C. R.; Li, W.; Doyle, A. G. J. Am. Chem. Soc. 2015, 137, 9571−9574.
[DOI: 10.1021/jacs.5b06307] Link PDF

PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent

30. Dialkyl Ether Formation via Nickel-Catalyzed Cross Coupling of Acetals and Aryl Iodides2020-09-22T00:50:44-07:00

Arendt, K. M.; Doyle, A. G. Angew. Chem. Int. Ed. 2015, 54, 9876-9880.
[DOI: 10.1002/anie.201503936] Link PDF

Dialkyl Ether Formation via Nickel-Catalyzed Cross Coupling of Acetals and Aryl Iodides

29. Electron-Deficient Olefin Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed Cross Coupling2020-09-22T00:51:21-07:00

Huang, C.-Y.; Doyle, A. G. J. Am. Chem. Soc. 2015, 137, 5638−5641.
[DOI: 10.1021/jacs.5b02503] Link PDF

Electron-Deficient Olefin Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed Cross Coupling

28. A Modular, Air-Stable Nickel Precatalyst2020-09-22T00:51:23-07:00

Shields, J. D.; Gray, E. E.; Doyle, A. G. Org. Lett. 2015, 17, 2166−2169.
[DOI: 10.1021/acs.orglett.5b00766] Link PDF

A Modular, Air-Stable Nickel Precatalyst

27. Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp3-carbons with aryl halides2022-12-30T15:51:05-08:00

Zuo, Z.; Ahneman, D.; Chu, L.; Terrett, J.; Doyle, A. G.; MacMillan, D. W. C.  Science. 2014, 345, 437-440.
[DOI: 10.1126/science.1255525] Link PDF

Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp3-carbons with aryl halides

26. The Chemistry of Transition Metals with Three-Membered Ring Heterocycles2020-09-22T00:51:30-07:00

Huang, C.-Y.; Doyle, A. G. Chem. Rev. 2014, 114, 8153-8198.
[DOI: 10.1021/cr500036t] Link PDF

The Chemistry of Transition Metals with Three-Membered Ring Heterocycles

25. Enantioselective radiosynthesis of positron emission tomography (PET) tracers containing [18F]fluorohydrins2020-09-22T00:51:36-07:00

Graham, T. J. A.; Lambert, R. F.; Ploessl, K.; Kung, H. F.; Doyle, A. G. J. Am. Chem. Soc. 2014, 136, 5291-5294.
[DOI: 10.1021/ja5025645] Link PDF

Enantioselective radiosynthesis of positron emission tomography (PET) tracers containing [18F]fluorohydrins

24. Mechanistic Investigations of Palladium-Catalyzed Allylic Fluorination2020-09-22T00:51:43-07:00

Katcher, M. H.; Norrby, P.-O.; Doyle, A. G.  Organometallics. 2014, 33, 2121-2133.
[DOI: 10.1021/om401240p] Link PDF

Mechanistic Investigations of Palladium-Catalyzed Allylic Fluorination

23. Enantioselective, Nickel-Catalyzed Suzuki Cross-Coupling of Quinolinium Ions2020-09-22T00:51:48-07:00

Shields, J. D.; Ahneman, D. T.; Graham, T. J. A.; Doyle, A. G. Org. Lett. 2014, 16, 142-145.
[DOI: 10.1021/ol4031364] Link PDF

Enantioselective, Nickel-Catalyzed Suzuki Cross-Coupling of Quinolinium Ions

22. Directed Nickel-Catalyzed Negishi Cross Coupling of Alkyl Aziridines2022-12-30T15:50:05-08:00

Nielsen, D. K.; Huang, C.-Y.; Doyle, A. G.  J. Am. Chem. Soc. 2013, 135, 13605–13609.
[DOI: 10.1021/ja407223g] Link PDF

Directed Nickel-Catalyzed Negishi Cross Coupling of Alkyl Aziridines

21. Palladium-Catalyzed Allylic C–H Fluorination2020-09-22T00:52:06-07:00

Braun, M.-G.; Doyle, A. G. J. Am. Chem. Soc. 2013, 135, 12990–12993.
[DOI: 10.1021/ja407223g] Link PDF

Palladium-Catalyzed Allylic C–H Fluorination

20. Nickel-Catalyzed Enantioselective Arylation of Pyridinium Ions: Harnessing an Iminium Ion Activation Mode2020-09-22T00:52:12-07:00

Chau, S. T.; Lutz, J. P.; Wu, K.; Doyle, A. G. Angew. Chem. Int. Ed. 2013, 52, 9153-9156.
[DOI: 10.1002/anie.201303994] Link PDF

Nickel-Catalyzed Enantioselective Arylation of Pyridinium Ions: Harnessing an Iminium Ion Activation Mode

19. Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis2022-12-30T15:46:02-08:00

Kalow, J. A.; Doyle, A. G. Tetrahedron. 2013, 69, 5702-5709.
[DOI: 10.1016/j.tet.2013.01.062] Link PDF

Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis

18. Carbofluorination via a palladium-catalyzed cascade reaction2022-12-30T15:43:28-08:00

Braun, M.-G.;‡ Katcher, M. H.;‡ Doyle, A. G. Chem. Sci. 2013, 4, 1216–1220. (‡ Equal contribution)
[DOI: 10.1039/C2SC22198E] Link PDF

Carbofluorination via a palladium-catalyzed cascade reaction

17. Mechanistic Investigation of the Nickel-Catalyzed Suzuki Reaction of N,O-Acetals: Evidence for Boronic Acid-Assisted Oxidative Addition and an Iminium Activation Pathway2020-09-22T00:52:29-07:00

Sylvester, K. T.;‡ Wu, K.;‡ Doyle, A. G. J. Am. Chem. Soc. 2012, 134, 16967-16970. (‡ Equal contribution)
[DOI: 10.1021/ja3079362] Link PDF

Mechanistic Investigation of the Nickel-Catalyzed Suzuki Reaction of N,O-Acetals: Evidence for Boronic Acid-Assisted Oxidative Addition and an Iminium Activation Pathway

16. Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines2020-09-22T00:52:34-07:00

Kalow, J. A.; Schmitt, D. E.; Doyle, A. G. Org. Chem. 2012, 77, 4177–4183.
[DOI: 10.1021/jo300433a] Link PDF

Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines

15. Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines2020-09-22T00:52:59-07:00

Huang, C.-Y.; Doyle, A. G. J. Am. Chem. Soc. 2012, 134, 9541–9544.
[DOI: 10.1021/ja3013825] Link PDF

Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines

14. Nickel-Catalyzed Cross-Coupling of Chromene Acetals and Boronic Acids2020-09-22T00:53:02-07:00

Graham, T. J. A.; Doyle, A. G. Org. Lett. 2012, 14, 1616–1619.
[DOI: 10.1021/ol300364s] Link PDF

Nickel-Catalyzed Cross-Coupling of Chromene Acetals and Boronic Acids

13. Fluoride Ring-Opening Kinetic Resolution of Terminal Epoxides: Preparation of (S)-2-Fluoro-1-Phenylethanol2020-09-22T00:53:07-07:00

Shaw, T. W.; Kalow, J. A.; Doyle, A. G. Org. Synth. 2012, 89, 9–18.
[DOI: 10.15227/orgsyn.089.0009] Link PDF

Fluoride Ring-Opening Kinetic Resolution of Terminal Epoxides: Preparation of (S)-2-Fluoro-1-Phenylethanol

12. Palladium-Catalyzed Regio- and Enantioselective Fluorination of Acyclic Allylic Halides2020-09-22T00:53:13-07:00

Katcher, M. H.; Sha, A.; Doyle, A. G. J. Am. Chem. Soc. 2011, 133, 15902–15905.
[DOI: 10.1021/ja206960k] Link PDF

Palladium-Catalyzed Regio- and Enantioselective Fluorination of Acyclic Allylic Halides

11. Mechanistic Investigations of Cooperative Catalysis in the Enantioselective Fluorination of Epoxides2020-09-22T00:53:19-07:00

Kalow, J. A.; Doyle, A. G. J. Am. Chem. Soc. 2011, 133, 16001–16012.
[DOI: 10.1021/ja207256s] Link PDF

Mechanistic Investigations of Cooperative Catalysis in the Enantioselective Fluorination of Epoxides

10. Nickel-Catalyzed Cross Coupling of Styrenyl Epoxides with Boronic Acids2020-09-22T00:53:24-07:00

Nielsen, D. K.; Doyle, A. G. Angew. Chem., Int. Ed. 2011, 50, 6056–6059.
[DOI: 10.1002/anie.201101191] Link PDF

Nickel-Catalyzed Cross Coupling of Styrenyl Epoxides with Boronic Acids

9. Transition Metal-Catalyzed Cross Coupling with N-Acyliminium Ions Derived from Quinolines and Isoquinolines2020-09-22T00:53:29-07:00

Graham, T. J. A.; Shields, J. D.; Doyle, A. G.Chem. Sci. 2011, 2, 980–984.
[DOI: 10.1039/c1sc00026h] Link PDF

Transition Metal-Catalyzed Cross Coupling with N-Acyliminium Ions Derived from Quinolines and Isoquinolines

8. Palladium-Catalyzed Asymmetric Synthesis of Allylic Fluorides2020-09-22T00:53:34-07:00

Katcher, M. H.; Doyle, A. G. J. Am. Chem. Soc. 2010, 132, 17402–17404.
[DOI: 10.1021/jacs.0c03125] Link PDF

Palladium-Catalyzed Asymmetric Synthesis of Allylic Fluorides

7. Enantioselective Ring Opening of Epoxides by Fluoride Anion Promoted by a Cooperative Dual Catalyst System2020-09-22T00:53:41-07:00

Kalow, J. A.; Doyle, A. G. J. Am. Chem. Soc. 2010, 132, 3268–3269.
[DOI: 10.1021/ja100161d] Link PDF

Enantioselective Ring Opening of Epoxides by Fluoride Anion Promoted by a Cooperative Dual Catalyst System

The Doyle Lab • Prof. Abigail Doyle
Saul Winstein Chair in Organic Chemistry
Department of Chemistry and Biochemistry, UCLA
3515 Molecular Science Building • Los Angeles, CA 90095
agdoyle@chem.ucla.edu • Phone: (310) 206-1036

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