2024
Cahoon, S. B.; Chapman, S. J.; Fiala, T. A.; Genzink, M. J.; Yoon, T. P. Development of a Highly Enantioselective Catalytic Di-π-methane Rearrangement. J. Org. Chem. 2024 in press.
Plachinski, E. F.; Qian, R. Z.; Villanueva, R.; Poole, D. L.; Rosenthal, T.; Yoon, T. P. Enantioselective [2π + 2σ] Photocycloaddition Enabled by Brønsted Acid Catalyzed Chromophore Activation, J. Am. Chem. Soc. 2024, in press.
Villanueva, R.; Plachinski, E. F.; Yoon, T. P. Synthesis of Benzyl-δ-truxinate via Enantioselective [2+2] Photocycloaddition, Org. Synth. 2024, 101,309–326.
Plachinski, E. F.; Yoon, T. P. Single-atom editing with light, Science 2024, 386, 27.
Meyer, A. R.; Popescu, M. R.; Sau, A.; Damrauer, N. H.; Paton, R. S.; Yoon, T. P. Combined Synthetic, Spectroscopic, and Computational Insights Into a General Method for Photosensitized Alkene Aziridination. ACS Catal. 2024, 14, 12310–12317.
Pal, Y.; Fiala, T. A.; Swords, W. B.; Yoon, T. P.; Schmidt, J. R. Predicting Emission Spectra of Heteroleptic Iridium Complexes Using Artificial Chemical Intelligence. ChemPhysChem 2024, in press.
Kidd, J. B.; Fiala, T. A.; Swords, W. B.; Park, Y.; Meyer K. A.; Sanders, K. M.; Guzei, I. A.; Wright, J. C.; Yoon, T. P. Enantioselective Paternò–Büchi Reactions: Strategic Application of a Triplet Rebound Mechanism for Asymmetric Photocatalysis. J. Am. Chem. Soc. 2024, 146, 15293–15300.
Plachinski, E. F.; Kim, H. J.; Genzink, M. J.; Sanders, K. M.; Kelch, R. M.; Guzei, I. A.; Yoon, T. P. A General Synthetic Strategy toward the Truxillate Natural Products via Solid-State Photocycloadditions. J. Am. Chem. Soc. 2024, 146, 14948–14953.
Lutovsky, G.; Yoon, T. P. Cu(II) salts as terminal oxidants in visible-light photochemical oxidation reactions. Org. Biomol. Chem. 2024, 22, 25–36.
2023
Swords, W. B.; Lee, H.; Park, Y.; Llamas, F.; Skubi, K. L.; Park, J.; Guzei, I. A.; Baik, M.-H.; Yoon, T. P. Highly Enantioselective 6π Photoelectrocyclizations Engineered by Hydrogen Bonding, J. Am. Chem. Soc. 2023, 145, 27045–270543.
Genzink, M. J.; Rossler, M. D.; Recendiz, H.; Yoon, T. P. A General Strategy for the Synthesis of Truxinate Natural Products Enabled by Enantioselective [2+2] Photocycloadditions. J. Am. Chem. Soc. 2023, 145, 19182–19188.
Lutovsky, G. A.; Plachinski, E. F.; Reed. N. L.; Yoon, T. P. Allylic Amination of Highly Substituted Alkenes Enabled by Photoredox Catalysis and Cu(II)-Mediated Radical–Polar Crossover. Org. Lett. 2023, 25, 4750–4754.
Kelch, R. M.; Whyte, A.; Lee, E.; Yoon, T. P. Investigating the Effect of Lewis Acid Co-catalysts on Photosensitized Visible-Light De Mayo Reactions, Org. Lett. 2023, 25, 4098–4102.
Lutovsky, G. A.; Gockel, S. N.; Bundesmann, M. W.; Bagley, S. W.; Yoon, T. P. Iron-mediated modular decarboxylative cross-nucleophile coupling, Chem 2023, 9, 1344–1346.
Swords, W. B.; Yoon, T. P. ” Transient absorption spectroscopy in visible-light photocatalysis,” in Specialist Periodical Reports: Photochemistry; Crespi, S., Protti, S., Eds; Royal Society of Chemistry: Corydon, 2023; Vol. 50, pp 428–457.
2022
Whyte, A.; Yoon, T. P. Selective Cross-Ketonization of Carboxylic Acids Enabled by Metallaphotoredox Catalysis. Angew. Chem. Int. Ed. 2022, 61, e202213739.
Girvin, Z. C.; Cotter, L. F.; Yoon, H.; Chapman, S. J.; Mayer, J. M.; Yoon, T. P. Miller, S. J. Asymmetric Photochemical [2 + 2]-Cycloaddition of Acyclic Vinylpyridines through Ternary Complex Formation and an Uncontrolled Sensitization Mechanism. J. Am. Chem. Soc. 2022, 144, 20109–20117.
Swords, W. B.; Chapman, S. J.; Hofstetter, H.; Dunn. A. L.; Yoon, T. P. Variable Temperature LED–NMR: Rapid Insights into a Photocatalytic Mechanism from Reaction Progress Kinetic Analysis. J. Org. Chem. 2022, 87, 11776–11782.
Chapman, S. J.; Swords, W. B.; Le, C. M.; Guzei, I. A.; Toste, F. D.; Yoon, T. P. Cooperative Stereoinduction in Asymmetric Photocatalysis. J. Am. Chem. Soc. 2022, 144, 4206–4213.
Li, Q.Y., Gockel, S.N., Lutovsky, G.A., DeGlopper, K. S.; Baldwin, N. J.; Bundesmann, M. W.; Tucker, J. W.; Bagley, S. W.; Yoon, T. P. Decarboxylative cross-nucleophile coupling via ligand-to-metal charge transfer photoexcitation of Cu(II) carboxylates. Nat. Chem. 2022, 14, 94–99.
2021
Genzink, M. J.; Kidd, J. B.; Swords, W. B.; Yoon, T. P. Chiral Photocatalyst Structures in Asymmetric Photochemical Synthesis, Chem. Rev. 2021, 112, 1654–1716.
Sherbrook, E. M.; Genzink, M. J.; Park, B.; Guzei, I. A.; Baik, M.-H.; Yoon, T. P. Chiral Brønsted acid-controlled intermolecular asymmetric [2 + 2] photocycloadditions, Nat. Commun. 2021, 12, 5735.
Dong, X.; Li, Q. Y.; Yoon, T. P. Enantioselective Synthesis of γ-Oxycarbonyl Motifs by Conjugate Addition of Photogenerated α-Alkoxy Radicals, Org. Lett. 2021, 23, 5803–5708.
Cahoon, S. B.; Yoon, T. P., Photochemistry and Radical Generation: Approaches in Mechanism Elucidation. In Science of Synthesis: Free Radicals: Fundamentals and Applications in Organic Synthesis, Fensterbank, L.; Ollivier, C., Eds.; Thieme: Stuttgart, (2021); Vol. 1, p 159-205.
Reed, N. L.; Lutovsky, G. A.; Yoon, T. P. Copper-Mediated Radical–Polar Crossover Enables Photocatalytic Oxidative Functionalization of Sterically Bulky Alkenes, J. Am. Chem. Soc. 2021, 143, 6065–6070.
Scholz, S. O.; Kidd, J. B.; Capaldo, L.; Flikweert, N. E.; Littlefield, R. M.; Yoon, T. P. Construction of Complex Cyclobutane Building Blocks by Photosensitized [2 + 2] Cycloaddition of Vinyl Boronate Esters, Org. Lett. 2021, 23, 3496–3501.
Reed, N. L.; Yoon, T. P. Oxidase Reactions in Photoredox Catalysis, Chem. Soc. Rev. 2021, 50, 2954–2967.
Gravatt, C. S.; Melecio-Zambrano, L.; Yoon, T. P. Olefin-Supported Cationic Copper Catalysts for Photochemical Synthesis of Structurally Complex Cyclobutanes, Angew. Chem. Int. Ed. 2021, 60, 3989–3993.
2020
Zheng, J.; Dong, X.; Yoon, T. P. Divergent Photocatalytic Reactions of α-Ketoesters under Triplet Sensitization and Photoredox Conditions, Org. Lett. 2020, 16, 6520–6525.
Skubi, K. L.; Swords, W. B.; Hofstetter, H.; Yoon, T. P. LED‐NMR Monitoring of an Enantioselective Catalytic [2+2] Photocycloaddition, ChemPhotoChem 2020, 4, 685–690.
Sherbrook, E. M.; Jung, H.; Cho, D.; Baik, M. H.; Yoon, T. P. Brønsted Acid Catalysis of Photosensitized Cycloadditions, Chem. Sci. 2020, 11, 856–861.
Lee, B. J.; DeGlopper, K. S.; Yoon, T. P. Site-Selective Alkoxylation of Benzylic C–H Bonds via Photoredox Catalysis. Angew. Chem. Int. Ed. 2020, 59, 197–202.
2019
Yoon, T. P. Stereocontrolled Photochemical Synthesis. ChemPhotoChem 2019, 3, 1201–1202.
Zheng, J.; Swords, W. B.; Jung, H.; Skubi, K. L.; Kidd, J. B.; Meyer, G. J.; Baik, M.-H.; Yoon, T. P. Enantioselective Intermolecular Excited-State Photoreactions Using a Chiral Ir Triplet Sensitizer: Separating Association from Energy Transfer in Asymmetric Photocatalysis. J. Am. Chem. Soc. 2019, 141, 13625–13634. [cover]
Daub, M. E.; Jung, H.; Lee, B. J.; Won, J.; Baik, M. H.; Yoon, T. P. Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer. J. Am. Chem. Soc. 2019, 141, 9543–9547.
Amador, A. G.; Sherbrook, E. M.; Yoon, T. P. A Redox Auxiliary Strategy for Pyrrolidine Synthesis via Photocatalytic [3+2] Cycloaddition. Asian J. Org. Chem. 2019, 8, 978–985.
Asymmetric Catalysis of Triplet-State Photoreactions. Photochemistry 2019, 46, 432-448.
Discovery And Elucidation Of Counteranion Dependence in Photoredox Catalysis. Journal of the American Chemical Society 2019, 141, 6385-6391.
Reed, N. L.; Herman, M. I.; Miltchev, V. P.; Yoon, T. P. Tandem Copper and Photoredox Catalysis in Photocatalytic Alkene Difunctionalization Reactions. Beilstein J. Org. Chem. 2019, 15, 351–356.
2018
A General Protocol For Radical Anion 3+2 Cycloaddition Enabled By Tandem Lewis Acid Photoredox Catalysis. Synthesis-Stuttgart 2018, 50, 539-547.
Photocatalytic Oxyamination Of Alkenes: Copper(II) Salts As Terminal Oxidants In Photoredox Catalysis. Organic Letters 2018, 20, 7345-7350.
Amador, A. G.; Scholz, S. O.; Skubi, K. L.; Yoon, T. P. Cycloadditions in Photocatalysis. In Science of Synthesis: Photocatalysis in Organic Synthesis, George Thieme Verlag KG, 2018; Vol. 1, pp 467–516
2017
Enantioselective Crossed Photocycloadditions Of Styrenic Olefins By Lewis Acid Catalyzed Triplet Sensitization. Angewandte Chemie-International Edition 2017, 56, 11891-11895.
Enantioselective Excited-State Photoreactions Controlled By A Chiral Hydrogen-Bonding Iridium Sensitizer. Journal of the American Chemical Society 2017, 139, 17186-17192.
Photocatalytic Indole Diels-Alder Cycloadditions Mediated By Heterogeneous Platinum-Modified Titanium Dioxide. ACS Catalysis 2017, 7, 6440-6444.
Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries. Organic Letters 2017, 19, 368-371.
Strategies In Asymmetric Catalysis. Beilstein Journal of Organic Chemistry 2017, 13, 63-64.
Titanium Dioxide Visible Light Photocatalysis: Surface Association Enables Photocatalysis With Visible Light Irradiation. Chemical Communications 2017, 53, 4335-4338.
2016
A Chiral Metal Photocatalyst Architecture For Highly Enantioselective Photoreactions. Angewandte Chemie-International Edition 2016, 55, 2304-2306.
Dual Catalysis Strategies In Photochemical Synthesis. Chemical Reviews (Washington, D. C.) 2016, 116, 10035-10074.
Editorial For The Special Issue On Photocatalysis. Journal of Organic Chemistry 2016, 81, 6895-6897.
Enantioselective Photocatalytic 3+2 Cycloadditions Of Aryl Cyclopropyl Ketones. Journal of the American Chemical Society 2016, 138, 4722-4725.
Enantioselective Photochemistry Through Lewis Acid-Catalyzed Triplet Energy Transfer. Science 2016, 354, 1391-1395.
Photochemical Stereocontrol Using Tandem Photoredox-Chiral Lewis Acid Catalysis. Accounts of Chemical Research 2016, 49, 2307-2315.
Spin-Selective Generation Of Triplet Nitrenes: Olefin Aziridination Through Visible-Light Photosensitization Of Azidoformates. Angewandte Chemie-International Edition 2016, 55, 2239-2242.
2015
Characterizing Chain Processes In Visible Light Photoredox Catalysis. Chemical Science 2015, 6, 5426-5434.
Enantioselective Conjugate Additions Of Alpha-Amino Radicals Via Cooperative Photoredox And Lewis Acid Catalysis. Journal of the American Chemical Society 2015, 137, 2452-2455.
An Improved Procedure For The Preparation Of Ru(Bpz)(3)(Pf6)(2) Via A High-Yielding Synthesis Of 2,2 ‘-Bipyrazine. Beilstein Journal of Organic Chemistry 2015, 11, 61-65.
2014
2+2 Cycloaddition Of 1,3-Dienes By Visible Light Photocatalysis. Angewandte Chemie-International Edition 2014, 53, 8991-8994.
3+2 Photooxygenation Of Aryl Cyclopropanes Via Visible Light Photocatalysis. Tetrahedron 2014, 70, 4270-4278.
Advances In The Chemistry Of Oxaziridines. Chemical Reviews 2014, 114, 8016-8036.
A Dual-Catalysis Approach To Enantioselective 2+2 Photocycloadditions Using Visible Light. Science 2014, 344, 392-396.
Iron-Catalyzed Kinetic Resolution Of N-Sulfonyl Oxaziridines. Chemical Science 2014, 5, 3524-3527.
Opportunities In Photocatalytic Synthesis. Advanced Synthesis & Catalysis 2014, 356, 2739-2739.
Organic Chemistry: Shape Control In Reactions With Light. Nature 2014, 515, 45-46.
Photocatalytic Synthesis Of Dihydrobenzofurans By Oxidative 3+2 Cycloaddition Of Phenols. Angewandte Chemie-International Edition 2014, 53, 11056-11059.
Redox Mediators In Visible Light Photocatalysis: Photocatalytic Radical Thiol-Ene Additions. Journal of Organic Chemistry 2014, 79, 1427-1436.
Solar Synthesis: Prospects In Visible Light Photocatalysis. Science 2014, 343, 985-+.
Visible-Light Sensitization Of Vinyl Azides By Transition-Metal Photocatalysis. Angewandte Chemie-International Edition 2014, 53, 793-797.
2013
Bronsted Acid Cocatalysts In Photocatalytic Radical Addition Of Alpha-Amino C-H Bonds Across Michael Acceptors. Journal of Organic Chemistry 2013, 78, 4107-4114.
Reductive Cyclizations Of Nitroarenes To Hydroxamic Acids By Visible Light Photoredox Catalysis. Synthesis-Stuttgart 2013, 45, 2699-2705.
Transition Metal Photoredox Catalysis Of Radical Thiol-Ene Reactions. Journal of Organic Chemistry 2013, 78, 2046-2050.
Visible Light Photocatalysis: The Development Of Photocatalytic Radical Ion Cycloadditions. ACS Catalysis 2013, 3, 895-902.
2012
Accessing The Synthetic Chemistry Of Radical Ions. European Journal of Organic Chemistry2012, 3359-3372.
Crossed Intermolecular 2+2 Cycloaddition Of Styrenes By Visible Light Photocatalysis. Chemical Science 2012, 3, 2807-2811.
Endoperoxide Synthesis By Photocatalytic Aerobic 2+2+2 Cycloadditions. Organic Letters 2012, 14, 1640-1643.
Iron Catalyzed Asymmetric Oxyamination Of Olefins. Journal of the American Chemical Society 2012, 134, 12370-12373.
Photocatalytic 2+2 Cycloadditions Of Enones With Cleavable Redox Auxiliaries. Organic Letters 2012, 14, 1110-1113.
Photolysis, Oh Reactivity And Ozone Reactivity Of A Proxy For Isoprene-Derived Hydroperoxyenals (Hpalds). Physical Chemistry Chemical Physics 2012, 14, 7276-7286.
Visible Light Photocatalysis Of 2+2 Styrene Cycloadditions By Energy Transfer. Angewandte Chemie-International Edition 2012, 51, 10329-10332.
Visible Light Photocatalysis Of Intramolecular Radical Cation Diels-Alder Cycloadditions. Tetrahedron Letters 2012, 53, 3073-3076.
2011
[3+2] Cycloadditions Of Aryl Cyclopropyl Ketones By Visible Light Photocatalysis. Journal of the American Chemical Society 2011, 133, 1162-1164.
Hydroxycarboxylic Acid-Derived Organosulfates: Synthesis, Stability, And Quantification In Ambient Aerosol. Environmental Science & Technology 2011, 45, 6468-6474.
Photocatalytic Reductive Cyclizations Of Enones: Divergent Reactivity Of Photogenerated Radical And Radical Anion Intermediates. Chemical Science 2011, 2, 2115-2119.
Radical Cation Diels–Alder Cycloadditions By Visible Light Photocatalysis. Journal of the American Chemical Society 2011, 133, 19350-19353.
2011
Lu, Z.; Shen, M.; Yoon, T. P. [3+2] Cycloadditions Of Aryl Cyclopropyl Ketones By Visible Light Photocatalysis. Journal of the American Chemical Society 2011, 133, 1162-1164.
Olson, C. N.; Galloway, M. M.; Yu, G.; Hedman, C. J.; Lockett, M. R.; Yoon, T. P.; Stone, E. A.; Smith, L. M.; Keutsch, F. N. Hydroxycarboxylic Acid-Derived Organosulfates: Synthesis, Stability, And Quantification In Ambient Aerosol. Environmental Science & Technology 2011, 45, 6468-6474.
Du, J.; Ruiz Espelt, L.; Guzei, I. A.; Yoon, T. P. Photocatalytic Reductive Cyclizations Of Enones: Divergent Reactivity Of Photogenerated Radical And Radical Anion Intermediates. Chemical Science 2011, 2, 2115-2119.
Lin, S.; Ischay, M. A.; Fry, C. G.; Yoon, T. P. Radical Cation Diels–Alder Cycloadditions By Visible Light Photocatalysis. Journal of the American Chemical Society 2011, 133, 19350-19353.
Visible Light Photocatalysis Of Radical Anion Hetero-Diels-Alder Cycloadditions. Tetrahedron 2011, 67, 4442-4448.
2010
[2+2] Cycloadditions By Oxidative Visible Light Photocatalysis. Journal of the American Chemical Society 2010, 132, 8572-+.
Carbonyl Imines From Oxaziridines: Generation And Cycloaddition Of N-O=C Dipoles. Angewandte Chemie-International Edition 2010, 49, 930-934.
Iron-Catalyzed Aminohydroxylation Of Olefins. Journal of the American Chemical Society2010, 132, 4570-+.
N-Nosyl Oxaziridines As Terminal Oxidants In Copper(Ii)-Catalyzed Olefin Oxyaminations. Tetrahedron Letters 2010, 51, 5223-5225.
Oxaziridine-Mediated Oxyamination Of Indoles: An Approach To 3-Aminoindoles And Enantiomerically Enriched 3-Aminopyrroloindolines. Angewandte Chemie-International Edition 2010, 49, 9153-9157.
Visible Light Photocatalysis As A Greener Approach To Photochemical Synthesis. Nature Chemistry 2010, 2, 527-532.
2009
Anionic Halocuprate(Ii) Complexes As Catalysts For The Oxaziridine-Mediated Aminohydroxylation Of Olefins. Journal of Organic Chemistry 2009, 74, 5545-5552.
Crossed Intermolecular [2+2] Cycloadditions Of Acyclic Enones Via Visible Light Photocatalysis. Journal of the American Chemical Society 2009, 131, 14604-+.
A Discussion Of “can Reaction Mechanisms Be Proven?”. Journal of Chemical Education 2009, 86, 557-557.
Oxaziridine-Mediated Enantioselective Aminohydroxylation Of Styrenes Catalyzed By Copper(Ii) Bis(Oxazoline) Complexes. Tetrahedron 2009, 65, 5118-5124.
Oxaziridine-Mediated Intramolecular Amination Of Sp(3)-Hybridized C-H Bonds. Journal of the American Chemical Society 2009, 131, 12560-12561.
2008
Activation Of N-Sulfonyl Oxaziridines Using Copper(Ii) Catalysts: Aminohydroxylations Of Styrenes And 1,3-Dienes. Journal of the American Chemical Society 2008, 130, 6610-6615.
Cycloadditions Of N-Sulfonyl Nitrones Generated By Lewis Acid Catalyzed Rearrangement Of Oxaziridines. Journal of the American Chemical Society 2008, 130, 2920-2921.
Efficient Visible Light Photocatalysis Of 2+2 Enone Cycloadditions. Journal of the American Chemical Society 2008, 130, 12886-+.
2007
Copper(Ii)-Catalyzed Aminohydroxylation Of Olefins. Journal of the American Chemical Society 2007, 129, 1866-+.
2005
Highly Enantioselective Thiourea-Catalyzed Nitro-Mannich Reactions. Angewandte Chemie-International Edition 2005, 44, 466-468.
2003
Privileged Chiral Catalysts. Science 2003, 299, 1691-1693.
2001
3,3-Dimethyl-2-Benzenesulfonyl Oxaziridine. In Encyclopedia of Reagents for Organic Synthesis; Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons, Ltd, 2001.
Enantioselective Claisen Rearrangements: Development Of A First Generation Asymmetric Acyl-Claisen Reaction. Journal of the American Chemical Society 2001, 123, 2911-2912.
1999
Development Of A New Lewis Acid-Catalyzed Claisen Rearrangement. Journal of the American Chemical Society 1999, 121, 9726-9727.
1995
Formation Of (Z) Dialkylboron Enolates From Enolsilanes: Stereoconvergent Transmetallation And Diastereoselective Aldol Reactions. Tetrahedron Letters 1995, 36, 9245-9248.