Publications

(44) Rybak, C. J.; Fan, C.; Sharma, P.; Uyeda, C. "Dinickel-Catalyzed N=N Coupling Reactions for the Synthesis of Hindered Azoarenes" J. Am. Chem. Soc. 2024, DOI: 10.1021/jacs.4c11061.

TOC_Hindered_Azide_Coupling.jpeg

(43) Liu, M.; Uyeda, C. "Redox Approaches to Carbene Generation in Catalytic Cyclopropanation Reactions" Angew. Chem. Int. Ed. 2024, 63, e202406218.

TOC_RedoxCarbeneMinireview.jpg

(42) Algera, R. F.; Allais, C.; Baldwin, A. F.; Busch, T.; Colombo, F.; Colombo, M.; Depretz, C.; Dumond, Y. R.; Faria Quintero, A. R.; Heredia, M.; Jung, J.; Lall, A.; Lee, T.; Liu, Y.; Mandelli, S.; Mantel, M.; Morris, R.; Mustakis, J.; Nguyen, B.; Pearson, R.; Piper, J. L.; Ragan, J. A.; Ruffin, B.; Talicska, C.; Tcyrulnikov, S.; Uyeda, C.; Weekly, R. M.; Zeng, M. "Synthesis of Nirmatrelvir: Development of a Scalable Cobalt-Catalyzed Cyclopropanation for Manufacture of the Bicyclic [3.1.0]Proline-Building Block" Org. Process Res. Dev. 2023, DOI: 10.1021/acs.oprd.3c00251.

TOC_OPRD_Pfizer.jpeg(41) Liu, M.; Le, N.; Uyeda, C. "Nucleophilic Carbenes Derived from Dichloromethane" Angew. Chem. Int. Ed. 2023, 62, e202308913.

TOC_Ni_Cyclopropanation.jpg

(40) Kanale, V. V.; Uyeda, C. "Catalytic Asymmetric Ring-Opening Reactions of Unstrained Heterocycles Using Cobalt Vinylidenes" Angew. Chem. Int. Ed. 2023, 62, e202309681.

TOC_Vinylidene_Ring_Opening.jpg

(39) Bishop, H. D.; Zhao, Q.; Uyeda, C. "Catalytic Asymmetric Synthesis of Zinc Metallacycles" J. Am. Chem. Soc. 2023, 145, 20152–20157.

TOC_Alkyne_Imine.jpeg

(38) Berger, K. E.; Martinez, R. J.; Zhou, J.; Uyeda, C. "Catalytic Asymmetric Cyclopropanations with Nonstabilized Carbenes" J. Am. Chem. Soc. 2023, 145, 94419447.

TOC_CoAsymmetricCyclopropanation.jpeg

(37) Rybak, C. J.; Andjaba, J. M.; Fan, C.; Zeller, M.; Uyeda, C. "Dinickel-Catalyzed N═N Bond Rotation" Inorg. Chem. 2023, 625886–5891.

TOC_NNrotation.jpeg

(36) Wang, Z.; Andjaba, J. M.; Rybak, C.; You, L.; Uyeda, C.; Mei, J. "Black-to-Transmissive dual polymer complementary electrochromics with high coloration efficiency" Chem. Eng. J. 2023, 456, 141013–141019.

TOC_CEJ.jpg

(35) Kalb, A. E.; Liu, M.; Bosso, M. I.; Uyeda, C. "A dinickel-catalyzed three-component cycloaddition of vinylidenes" Chem. Sci. 2022, 13, 1119011196.

 toc_aldehyde.bmp

(34) Uyeda, C.; Kalb, A. E. "Catalytic reductive carbene transfer reactions" Chem Catalysis 2022, 2, 667–678. 

TOC_CatalyticReductiveCarbene.jpg

(33) Steiman, T. J.; Kalb, A. E.; Coombs, J. C.; Kirkland, J. K.; Torres, H.; Ess, D. H.; Uyeda, C. "Dinickel-Catalyzed Vinylidene–Alkene Cyclization Reactions" ACS Catal. 2021, 11, 14408–14416.

TOC_Vinylidene_C-Hinsertion.jpeg

(32) Uyeda, C.; Farley, C. M. "Dinickel Active Sites Supported by Redox-Active Ligands." Acc. Chem. Res. 2021, 54, 3710–3719.

TOC_Dinickel_Review_2021.jpeg

(31) Andjaba, J. M.; Rybak, C. J.; Wang, Z.; Ling, J.; Mei, J.; Uyeda, C. "Catalytic Synthesis of Conjugated Azopolymers from Aromatic Diazides" J. Am. Chem. Soc. 2021, 143, 39753982.

(30) Kang, H.; Uyeda, C. "Nickel-Catalyzed Vinylidene Insertions into O–H Bonds" ACS Catal. 2021, 11, 193198.

(29) Maity, A. K.; Kalb, A. E.; Zeller, M.; Uyeda, C. "A Dinickel Catalyzed Cyclopropanation without the Formation of a Metal Carbene Intermediate" Angew. Chem. Int. Ed. 2020, 60, 18971902.

TOC_Diazocyclopropanation.jpg

(28) Biswas, S.; Pal, S.; Uyeda, C. "Nickel-catalyzed insertions of vinylidenes into Si–H bonds" Chem. Commun. 2020, 5614175–14178.

[Invited Contribution to a Themed Collection: 2020 Emerging Investigators]

 TOC_Si-H-insertion.png

(27) Powers, I. G.; Andjaba, J. M.; Zeller, M.; Uyeda, C. "Catalytic C(sp2)-H Amination Reactions Using Dinickel Imides" Organometallics 2020, 39, 3794–3801.

OM-CH-amination

(26) Behlen, M. and Uyeda, C. "C2-Symmetric Dinickel Catalysts for Enantioselective [4 + 1]-Cycloadditions" J. Am. Chem. Soc. 2020142, 17294-17300.

TIC-MB

(25) Farley, C; Sasakura, K. Zhou, Y.-Y.; Kanale, V; Uyeda, C. "Catalytic [5 + 1]-Cycloadditions of Vinylcyclopropanes and Vinylidenes" J. Am. Chem. Soc. 2020142, 4598-4603.

TIC-JW

(24) Werth, J.; Berger, K.; Uyeda, C. "Cobalt Catalyzed Reductive Spirocyclopropanation Reactions" Adv. Synth. Catal. 2019, 362, 348-352.

TIC-JW

(23) Farley, C.; Uyeda, C. "Organic Reactions Enabled by Catalytically Active Metal–Metal Bonds" Trends in Chemistry 2019, 497-509.

JACS-CF

(22) Adolph, C.; Lee, S.; Uyeda, C. "Dinickel catalyzed carbonylation reactions using metal carbonyl reagents as CO sources" Tetrahedron 2019, 75, 3336–3340. 

JACS-CF

(21) Zhou, Y.-Y.; Uyeda, C. "Catalytic reductive [4 + 1]-cycloadditions of vinylidenes and dienes" Science 2019, 363, 857-862.

JACS-CF

(20) Farley, C. F.; Zhou, Y.-Y.; Banka, N.; Uyeda, C. "Catalytic Cyclooligomerization of Enones with Three Methylene Equivalents" J. Am. Chem. Soc. 2018, DOI: 10.1021/jacs.8b08296

JACS-CF

(19) Werth, J.; Uyeda, C. "Cobalt Catalyzed Reductive Dimethylcyclopropanation of 1,3‐Dienes" Angew. Chem. Int. Ed. 2018, DOI: 10.1002/anie.201807542

ACIE-2018

(18) Maity, A. K.; Zeller, M.; Uyeda, C. "Carbene Formation and Transfer at a Dinickel Active Site" Organometallics 2018, 37, 2437-2441.

OM-2018

(17) Powers, I. G.; Andjaba, J. M.; Luo, X.; Mei, J.; Uyeda, C. "Catalytic Azoarene Synthesis from Aryl Azides Enabled by a Dinuclear Ni Complex." J. Am. Chem. Soc. 2018, 140, 4110-4118.

JACS-2018

(16) Rounds, H. R.; Zeller, M.; Uyeda, C. "Dinuclear Pathways for the Activation of Strained Three-Membered Rings." Organometallics 2018, 37, 545–550.

OM-TOC-2018

(15) Werth, J.; Uyeda, C. "Regioselective Simmons-Smith-Type Cyclopropanations of Polyalkenes Enabled by Transition Metal Catalysis" Chem. Sci. 2018, 9, 1604-1609.

ChemSci-2018

(14) Hartline, D. R.; Zeller, M. Uyeda, C. "Catalytic Carbonylative Rearrangement of Norbornadiene via Dinuclear CarbonCarbon Oxidative Addition" J. Am. Chem. Soc. 2017139, 13672-13675.

Norbornadiene

(13) Pal, S.; Zhou, Y.-Y.; Uyeda, C. "Catalytic Reductive Vinylidene Transfer Reactions" J. Am. Chem. Soc. 2017, 13911686–11689.

JACS-TOC

(12) Kwon, D.-H.; Proctor, M.; Mendoza, S.; Uyeda, C.; Ess, D. H. "Catalytic Dinuclear Nickel Spin Crossover Mechanism and Selectivity for Alkyne Cyclotrimerization" ACS Catal. 2017, 7, 4796-4804.

ESS-TOC

(11) Steiman, T. J.; Uyeda, C. "Dinickel, 1,1(-(1,8-Naphthyridine-2,7-diyl)bis[N-(2,6-diisopropylphenyl)ethan-1-imine](benzene)" e-EROS 2017.

ESS-TOC

(10) Adolph, C. M.; Werth, J.; Selvaraj, R; Wegener, E. C.; Uyeda, C. "Dehydrogenative Transformations of Imines Using a Heterogeneous Photocatalyst" J. Org. Chem. 2017, 82, 5959–5965.

TOC-JOC-2017

(9) Powers, I. G.; Kiattisewee, C.; Mullane, K. C.; Schelter, E. J.; Uyeda, C. "A 1,2-Addition Pathway for C(sp2)–H Activation at a Dinickel Imide" Chem. Eur. J. 2017, 23, 7694–7697.

ChemEurJ-2017-TOC

(8) Powers, I. G.; Uyeda, C. "Metal-Metal Bonds in Catalysis" ACS Catalysis. 2017, 7, 936-958. 

acsCatal1.jpg

(7) Behlen, M. J.; Zhou, Y.-Y.; Steiman, T. J.; Pal, S.; Hartline, D. R.; Zeller, M.; Uyeda, C. "Dinuclear Oxidative Addition Reactions Using an Isostructural Series of Ni2, Co2, and Fe2 Complexes" Dalton Trans. 201746, 5493-5497. 

      [Invited Contribution to a Themed Issue "Multimetallic Complexes: Synthesis and Applications"]

Dalton-2016

(6) Hartline, D. R.; Zeller, M.; Uyeda, C. "Well-Defined Models for the Elusive Dinuclear Intermediates of the Pauson-Khand Reaction." Angew. Chem. Int. Ed. 2016, 128 (20), 6188-6191. 

PKR

(5) Zhou, Y.-Y.; Uyeda, C. "Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes." Angew. Chem. Int. Ed. 2016128 (9), 3223-3227.

pubs-2016-ACIE

(4) Uyeda, C.; Steiman, T. J.; Pal, S. "Catalytically Active Nickel–Nickel Bonds Using Redox-Active Ligands" Synlett 201627 (06), 814-820.

      [Invited Contribution: Synpacts]

Pubs-2016-Synlett

(3) Pal, S.; Uyeda, C. "Evaluating the Effect of Catalyst Nuclearity in Ni-Catalyzed Alkyne Cyclotrimerizations." J. Am. Chem. Soc. 2015, 137 (25), 8042-8045.

Evaluating the Effect of Catalyst Nuclearity

(2) Steiman, T. J.; Uyeda, C. "Reversible Substrate Activation and Catalysis at an Intact Metal-Metal Bond Using a Redox-Active Supporting Ligand." J. Am. Chem. Soc. 2015, 137 (18), 6104-6110.

Reversible substrate activation

(1) Zhou, Y.-Y.; Hartline, D. R.; Steiman, T. J.; Fanwick, P. E.; Uyeda, C. "Dinuclear Nickel Complexes in Five States of Oxidation Using a Redox-Active Ligand." Inorg. Chem. 2014, 53 (21), 11770-11777.

pub-2014-IC


Previous Publications

(11) Huo, P.; Uyeda, C.; Goodpaster, J. D.; Peters, J. C.; Miller III, T. F. "Breaking the Correlation between Energy Costs and Kinetic Barriers in Hydrogen Evolution via a Cobalt Pyridine-Diimine-Dioxime Catalyst." ACS Catal. 20166, 6114-6123.

(10) Uyeda, C.; Peters, J. C. "Selective Nitrite Reduction at Heterobimetallic CoMg Complexes." J. Am. Chem. Soc. 2013, 135, 12023–12031.

(9) Uyeda, C.; Tan, Y.; Fu, G. C.; Peters, J. C. "A New Family of Nucleophiles for Photoinduced, Copper-Catalyzed Cross-Couplings via Single-Electron Transfer: Reactions of Thiols with Aryl Halides Under Mild Conditions (0 °C)." J. Am. Chem. Soc. 2013, 135, 9548–9552.

(8) Brown, A. R.; Uyeda, C.; Brotherton, C. A.; Jacobsen, E. N. "Enantioselective Thiourea-Catalyzed Intramolecular Cope-Type Hydroamination." J. Am. Chem. Soc. 2013, 135, 6747-6749.

(7) Uyeda, C.; Peters, J. C. "Access to Formally Ni(I) States in a Heterobimetallic NiZn System." Chem. Sci. 2013, 4, 157-163.

(6) McCrory, C. C. L.; Uyeda, C.; Peters, J. C. "Electrocatalytic Hydrogen Evolution in Acidic Water with Molecular Cobalt Tetraazamacrocycles." J. Am. Chem. Soc. 2012, 134, 3164-3170.

(5) Uyeda, C.; Jacobsen, E. N. "Transition-State Charge Stabilization through Multiple Non-Covalent Interactions in the Guanidinium-Catalyzed Enantioselective Claisen Rearrangement." J. Am. Chem. Soc. 2011, 133, 5062-5075.

(4) Uyeda, C.; Rötheli, A. R.; Jacobsen, E. N. “Catalytic Enantioselective Claisen Rearrangements of O-Allyl β-Ketoesters.” Angew. Chem. Int. Ed. 2010, 122, 9947–9950.

(3) Uyeda, C.; Jacobsen, E. N. "Enantioselective Claisen Rearrangements with a Hydrogen-Bond Donor Catalyst." J. Am. Chem. Soc. 2008, 130, 9228-9229.

(2) Uyeda, C.; Biscoe, M. R.; LePlae, P.; Breslow, R. "Hydrophobically Directed Selective Reduction of Ketones Using Amine Boranes." Tetrahedron, 2006, 47, 127-130.

(1) Biscoe, M. R.; Uyeda, C.; Breslow, R. "Requirements for Selective Hydrophobic Acceleration in the Reduction of Ketones." Org. Lett. 2004, 6, 4331-4334.