Leveraging ligand-based proton and electron transfer for aerobic reactivity and catalysis

Jesse, Kate A.; Anderson, John S.

doi:10.1039/D4SC03896G

Title: Leveraging ligand-based proton and electron transfer for aerobic reactivity and catalysis

Journal Article · 17 October 2024 · Chemical Science

DOI: https://doi.org/10.1039/D4SC03896G · OSTI ID:2453929

^[1];

^[2]

Los Alamos National Laboratory, Los Alamos, NM, 87545, USA
Department of Chemistry, The University of Chicago, Chicago, Illinois, 60637, USA

O ₂ is an attractive oxidant but it is also kinetically inert which limits its use in synthetic transformations. Metal–ligand cooperativity is a promising biomimetic strategy to activate O ₂ for oxidative reactivity and catalysis.

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Sponsoring Organization:: USDOE

OSTI ID:: 2453929

Journal Information:: Chemical Science, Journal Name: Chemical Science Journal Issue: 40 Vol. 15; ISSN 2041-6520; ISSN CSHCBM

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

References (106)

Aerobic Oxidation of Primary Alcohols by a New Mononuclear CuII-Radical Catalyst Chaudhuri, Phalguni; Hess, Martina; Weyhermüller, Thomas Angewandte Chemie International Edition, Vol. 38, Issue 8 https://doi.org/10.1002/(SICI)1521-3773(19990419)38:8<1095::AID-ANIE1095>3.0.CO;2-I	journal	April 1999
Organocatalytic Oxidations Mediated by Nitroxyl Radicals Sheldon, Roger A.; Arends, Isabel W. C. E. Advanced Synthesis & Catalysis, Vol. 346, Issue 910, p. 1051-1071 https://doi.org/10.1002/adsc.200404110	journal	August 2004
Katalytische Umsetzungen von Olefinen an Platinmetall-Verbindungen Das Consortium-Verfahren zur Herstellung von Acetaldehyd Smidt, J.; Hafner, W.; Jira, R. Angewandte Chemie, Vol. 71, Issue 5 https://doi.org/10.1002/ange.19590710503	journal	March 1959
Quercetin‐2,4‐Dioxygenase aktiviert Sauerstoff in einem “side‐on” gebundenen O₂‐Ni‐Komplex Jeoung, Jae‐Hun; Nianios, Dimitrios; Fetzner, Susanne Angewandte Chemie, Vol. 128, Issue 10 https://doi.org/10.1002/ange.201510741	journal	February 2016
C−H and C−N Activation at Redox-Active Pyridine Complexes of Iron MacLeod, K. Cory; Lewis, Richard A.; DeRosha, Daniel E. Angewandte Chemie, Vol. 129, Issue 4 https://doi.org/10.1002/ange.201610679	journal	December 2016
Reversible Binding of Dioxygen by a Non‐Transition‐Metal Complex Abakumov, Gleb A.; Poddel'sky, Andrey I.; Grunova, Ekaterina V. Angewandte Chemie International Edition, Vol. 44, Issue 18 https://doi.org/10.1002/anie.200462503	journal	April 2005
The Mechanism of the Wacker Reaction: A Tale of Two Hydroxypalladations Keith, John��A.; Henry, Patrick��M. Angewandte Chemie International Edition, Vol. 48, Issue 48 https://doi.org/10.1002/anie.200902194	journal	November 2009
Metal‐Free, Aerobic Dioxygenation of Alkenes Using Hydroxamic Acids Schmidt, Valerie A.; Alexanian, Erik J. Angewandte Chemie International Edition, Vol. 49, Issue 26 https://doi.org/10.1002/anie.201000843	journal	June 2010
Distinct Reactivity Differences of Metal Oxo and Its Corresponding Hydroxo Moieties in Oxidations: Implications from a Manganese(IV) Complex Having Dihydroxide Ligand Shi, Song; Wang, Yujuan; Xu, Aihua Angewandte Chemie International Edition, Vol. 50, Issue 32 https://doi.org/10.1002/anie.201100588	journal	June 2011
Acid‐Triggered O−O Bond Heterolysis of a Nonheme Fe ^III (OOH) Species for the Stereospecific Hydroxylation of Strong C−H Bonds Serrano‐Plana, Joan; Acuña‐Parés, Ferran; Dantignana, Valeria Chemistry – A European Journal, Vol. 24, Issue 20 https://doi.org/10.1002/chem.201704851	journal	January 2018
Ligand-Based Storage of Protons and Electrons in Dihydrazonopyrrole Complexes of Nickel Chang, Mu-Chieh; McNeece, Andrew J.; Hill, Ethan A. Chemistry - A European Journal, Vol. 24, Issue 31 https://doi.org/10.1002/chem.201800658	journal	May 2018
Reversible Binding of Molecular Oxygen to Catecholate and Amidophenolate Complexes of Sb^V: Electronic and Steric Factors Fukin, Georgy K.; Baranov, Evgenii V.; Poddel'sky, Andrey I. ChemPhysChem, Vol. 13, Issue 17 https://doi.org/10.1002/cphc.201200728	journal	October 2012
Mimicking the Reactivity of LPMOs with a Mononuclear Cu Complex Sagar, Kundan; Kim, Michael; Wu, Tong European Journal of Inorganic Chemistry, Vol. 27, Issue 15 https://doi.org/10.1002/ejic.202300774	journal	January 2024
Iron(II) Complexes Featuring a Redox‐Active Dihydrazonopyrrole Ligand Jesse, Kate A.; Chang, Mu‐Chieh; Filatov, Alexander S. Zeitschrift für anorganische und allgemeine Chemie, Vol. 647, Issue 14 https://doi.org/10.1002/zaac.202100097	journal	June 2021
Oxygen activation by mononuclear Mn, Co, and Ni centers in biology and synthetic complexes Fiedler, Adam T.; Fischer, Anne A. JBIC Journal of Biological Inorganic Chemistry, Vol. 22, Issue 2-3 https://doi.org/10.1007/s00775-016-1402-7	journal	November 2016
Oxygen activation by cytochrome P450 monooxygenase Hamdane, Djemel; Zhang, Haoming; Hollenberg, Paul Photosynthesis Research, Vol. 98, Issue 1-3 https://doi.org/10.1007/s11120-008-9322-1	journal	July 2008
Multiple mechanisms and multiple oxidants in P450-catalyzed hydroxylations Newcomb, Martin; Hollenberg, Paul F.; Coon, Minor J. Archives of Biochemistry and Biophysics, Vol. 409, Issue 1 https://doi.org/10.1016/S0003-9861(02)00445-9	journal	January 2003
Mechanism of the wacker process. Stereochemistry of the hydroxypalladation Stille, J. K.; Divakaruni, R. Journal of Organometallic Chemistry, Vol. 169, Issue 2 https://doi.org/10.1016/S0022-328X(00)81163-8	journal	April 1979
Oxygen activating nonheme iron enzymes Lange, Steven J.; Que, Lawrence Current Opinion in Chemical Biology, Vol. 2, Issue 2 https://doi.org/10.1016/S1367-5931(98)80057-4	journal	April 1998
Selective aerobic oxidation promoted by highly efficient multi-nitroxy organocatalysts Chen, Kexian; Xie, Haiying Chinese Journal of Catalysis, Vol. 38, Issue 4 https://doi.org/10.1016/S1872-2067(17)62777-3	journal	April 2017
Reductive elimination of superoxide: Structure and mechanism of superoxide reductases Pinto, Ana Filipa; Rodrigues, João V.; Teixeira, Miguel Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics, Vol. 1804, Issue 2 https://doi.org/10.1016/j.bbapap.2009.10.011	journal	February 2010
Three oxidation states of the bis(3,5-di-tert-butyl-2-phenolato)azanido pincer ligand on chromium(III) Hollas, Aaron M.; Ziller, Joseph W.; Heyduk, Alan F. Polyhedron, Vol. 143 https://doi.org/10.1016/j.poly.2017.08.043	journal	March 2018
Aerobic oxidation of secondary benzylic alcohols and direct oxidative amidation of aryl aldehydes promoted by sodium hydride Wang, Xinbo; Wang, David Zhigang Tetrahedron, Vol. 67, Issue 19 https://doi.org/10.1016/j.tet.2011.03.052	journal	May 2011
3d Metal Complexes in T-shaped Geometry as a Gateway to Metalloradical Reactivity Ott, Jonas C.; Bürgy, David; Guan, Hairong Accounts of Chemical Research, Vol. 55, Issue 6 https://doi.org/10.1021/acs.accounts.1c00737	journal	February 2022
Hydrogenation and Dehydrogenation Iron Pincer Catalysts Capable of Metal–Ligand Cooperation by Aromatization/Dearomatization Zell, Thomas; Milstein, David Accounts of Chemical Research, Vol. 48, Issue 7 https://doi.org/10.1021/acs.accounts.5b00027	journal	June 2015
Molecular Designs for Controlling the Local Environments around Metal Ions Cook, Sarah A.; Borovik, A. S. Accounts of Chemical Research, Vol. 48, Issue 8 https://doi.org/10.1021/acs.accounts.5b00212	journal	July 2015
Free Energies of Proton-Coupled Electron Transfer Reagents and Their Applications Agarwal, Rishi G.; Coste, Scott C.; Groff, Benjamin D. Chemical Reviews, Vol. 122, Issue 1 https://doi.org/10.1021/acs.chemrev.1c00521	journal	December 2021
Designing Artificial Metalloenzymes by Tuning of the Environment beyond the Primary Coordination Sphere Van Stappen, Casey; Deng, Yunling; Liu, Yiwei Chemical Reviews, Vol. 122, Issue 14 https://doi.org/10.1021/acs.chemrev.2c00106	journal	July 2022
Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions Wang, Dian; Weinstein, Adam B.; White, Paul B. Chemical Reviews, Vol. 118, Issue 5 https://doi.org/10.1021/acs.chemrev.7b00334	journal	October 2017
Dioxygen Activation by Nonheme Diiron Enzymes: Diverse Dioxygen Adducts, High-Valent Intermediates, and Related Model Complexes Jasniewski, Andrew J.; Que, Lawrence Chemical Reviews, Vol. 118, Issue 5 https://doi.org/10.1021/acs.chemrev.7b00457	journal	December 2017
Oxygen Reduction by Homogeneous Molecular Catalysts and Electrocatalysts Pegis, Michael L.; Wise, Catherine F.; Martin, Daniel J. Chemical Reviews, Vol. 118, Issue 5 https://doi.org/10.1021/acs.chemrev.7b00542	journal	December 2017
Same Substrate, Many Reactions: Oxygen Activation in Flavoenzymes Romero, Elvira; Gómez Castellanos, J. Rubén; Gadda, Giovanni Chemical Reviews, Vol. 118, Issue 4 https://doi.org/10.1021/acs.chemrev.7b00650	journal	January 2018
Metal-Ion Influence on Ligand-Centered Hydrogen-Atom Transfer Charette, Bronte J.; Ziller, Joseph W.; Heyduk, Alan F. Inorganic Chemistry, Vol. 60, Issue 3 https://doi.org/10.1021/acs.inorgchem.0c02981	journal	January 2021
Exploring Ligand-Centered Hydride and H-Atom Transfer Charette, Bronte J.; Ziller, Joseph W.; Heyduk, Alan F. Inorganic Chemistry, Vol. 60, Issue 7 https://doi.org/10.1021/acs.inorgchem.1c00351	journal	March 2021
Standard Reduction Potentials for Oxygen and Carbon Dioxide Couples in Acetonitrile and N , N -Dimethylformamide Pegis, Michael L.; Roberts, John A. S.; Wasylenko, Derek J. Inorganic Chemistry, Vol. 54, Issue 24 https://doi.org/10.1021/acs.inorgchem.5b02136	journal	December 2015
Reversible Redox Chemistry and Catalytic C(sp ³ )–H Amination Reactivity of a Paramagnetic Pd Complex Bearing a Redox-Active o -Aminophenol-Derived NNO Pincer Ligand Broere, Daniël L. J.; van Leest, Nicolaas P.; de Bruin, Bas Inorganic Chemistry, Vol. 55, Issue 17 https://doi.org/10.1021/acs.inorgchem.6b01192	journal	August 2016
Redox-Active Bis(phenolate) N-Heterocyclic Carbene [OCO] Pincer Ligands Support Cobalt Electron Transfer Series Spanning Four Oxidation States Harris, Caleb F.; Bayless, Michael B.; van Leest, Nicolaas P. Inorganic Chemistry, Vol. 56, Issue 20 https://doi.org/10.1021/acs.inorgchem.7b01906	journal	October 2017
Redox Noninnocent Azo-Aromatic Pincers and Their Iron Complexes. Isolation, Characterization, and Catalytic Alcohol Oxidation Sinha, Suman; Das, Siuli; Sikari, Rina Inorganic Chemistry, Vol. 56, Issue 22 https://doi.org/10.1021/acs.inorgchem.7b02238	journal	November 2017
cis Donor Influence on O–O Bond Lability in Iron(III) Hydroperoxo Complexes: Oxidation Catalysis and Ligand Transformation Wegeberg, Christina; Browne, Wesley R.; McKenzie, Christine J. Inorganic Chemistry, Vol. 58, Issue 14 https://doi.org/10.1021/acs.inorgchem.9b00247	journal	June 2019
Ruthenium-Chelated Non-Innocent Bis(heterocyclo)methanides: A Mimicked β-Diketiminate Panda, Sanjib; Bera, Sudip Kumar; Goel, Puneet Inorganic Chemistry, Vol. 58, Issue 17 https://doi.org/10.1021/acs.inorgchem.9b01201	journal	August 2019
Characterization of Terminal Iron(III)–Oxo and Iron(III)–Hydroxo Complexes Derived from O ₂ Activation Gordon, Zachary; Miller, Tabitha J.; Leahy, Clare A. Inorganic Chemistry, Vol. 58, Issue 23 https://doi.org/10.1021/acs.inorgchem.9b02079	journal	November 2019
Cobalt-Catalyzed Hydrogenation Reactions Enabled by Ligand-Based Storage of Dihydrogen Anferov, Sophie W.; Filatov, Alexander S.; Anderson, John S. ACS Catalysis, Vol. 12, Issue 16 https://doi.org/10.1021/acscatal.2c02467	journal	August 2022
Graphene Oxide: A Convenient Metal-Free Carbocatalyst for Facilitating Aerobic Oxidation of 5-Hydroxymethylfurfural into 2, 5-Diformylfuran Lv, Guangqiang; Wang, Hongliang; Yang, Yongxing ACS Catalysis, Vol. 5, Issue 9 https://doi.org/10.1021/acscatal.5b01446	journal	August 2015
Electrochemical Oxidation of Alcohols and Aldehydes to Carboxylic Acids Catalyzed by 4-Acetamido-TEMPO: An Alternative to “Anelli” and “Pinnick” Oxidations Rafiee, Mohammad; Konz, Zachary M.; Graaf, Matthew D. ACS Catalysis, Vol. 8, Issue 7 https://doi.org/10.1021/acscatal.8b01640	journal	May 2018
High-Potential Electrocatalytic O ₂ Reduction with Nitroxyl/NO _x Mediators: Implications for Fuel Cells and Aerobic Oxidation Catalysis Gerken, James B.; Stahl, Shannon S. ACS Central Science, Vol. 1, Issue 5 https://doi.org/10.1021/acscentsci.5b00163	journal	July 2015
Bioinspired Hydrogen Bond Motifs in Ligand Design: The Role of Noncovalent Interactions in Metal Ion Mediated Activation of Dioxygen Borovik, A. S. Accounts of Chemical Research, Vol. 38, Issue 1 https://doi.org/10.1021/ar030160q	journal	January 2005
Geometric and Electronic Structure Contributions to Function in Non-heme Iron Enzymes Solomon, Edward I.; Light, Kenneth M.; Liu, Lei V. Accounts of Chemical Research, Vol. 46, Issue 11 https://doi.org/10.1021/ar400149m	journal	July 2013
Understanding How the Thiolate Sulfur Contributes to the Function of the Non-Heme Iron Enzyme Superoxide Reductase Kovacs, Julie A.; Brines, Lisa M. Accounts of Chemical Research, Vol. 40, Issue 7 https://doi.org/10.1021/ar600059h	journal	May 2007
Development of Molecular Electrocatalysts for CO₂ Reduction and H₂ Production/Oxidation Rakowski Dubois, M.; Dubois, Daniel L. Accounts of Chemical Research, Vol. 42, Issue 12, p. 1974-1982 https://doi.org/10.1021/ar900110c	journal	December 2009
Mechanism of Oxidation Reactions Catalyzed by Cytochrome P450 Enzymes Meunier, Bernard; de Visser, Samuël P.; Shaik, Sason Chemical Reviews, Vol. 104, Issue 9 https://doi.org/10.1021/cr020443g	journal	September 2004
Dioxygen Activation at Mononuclear Nonheme Iron Active Sites: Enzymes, Models, and Intermediates Costas, Miquel; Mehn, Mark P.; Jensen, Michael P. Chemical Reviews, Vol. 104, Issue 2 https://doi.org/10.1021/cr020628n	journal	February 2004
Redox Non-Innocent Ligands: Versatile New Tools to Control Catalytic Reactions Lyaskovskyy, Volodymyr; de Bruin, Bas ACS Catalysis, Vol. 2, Issue 2 https://doi.org/10.1021/cs200660v	journal	January 2012
The Electronic Structure of Non-Heme Iron(III)−Hydroperoxo and Iron(III)−Peroxo Model Complexes Studied by Mössbauer and Electron Paramagnetic Resonance Spectroscopies Simaan, A. Jalila; Banse, Frédéric; Girerd, Jean-Jacques Inorganic Chemistry, Vol. 40, Issue 26 https://doi.org/10.1021/ic010635e	journal	November 2001
Investigation of the Mechanism of Formation of a Thiolate-Ligated Fe(III)-OOH Nam, Elaine; Alokolaro, Pauline E.; Swartz, Rodney D. Inorganic Chemistry, Vol. 50, Issue 5 https://doi.org/10.1021/ic101776m	journal	February 2011
Manifestations of Noninnocent Ligand Behavior Kaim, Wolfgang Inorganic Chemistry, Vol. 50, Issue 20 https://doi.org/10.1021/ic2003832	journal	October 2011
A Functional Model for the Cysteinate-Ligated Non-Heme Iron Enzyme Superoxide Reductase (SOR) Kitagawa, Terutaka; Dey, Abhishek; Lugo-Mas, Priscilla Journal of the American Chemical Society, Vol. 128, Issue 45 https://doi.org/10.1021/ja064870d	journal	October 2006
Catalytic Reduction of Dioxygen to Water with a Monomeric Manganese Complex at Room Temperature Shook, Ryan L.; Peterson, Sonja M.; Greaves, John Journal of the American Chemical Society, Vol. 133, Issue 15 https://doi.org/10.1021/ja106564a	journal	April 2011
Characterization of a High-Spin Non-Heme Fe ^III –OOH Intermediate and Its Quantitative Conversion to an Fe ^IV ═O Complex Li, Feifei; Meier, Katlyn K.; Cranswick, Matthew A. Journal of the American Chemical Society, Vol. 133, Issue 19 https://doi.org/10.1021/ja111742z	journal	May 2011
Metal-Free, Aerobic Dioxygenation of Alkenes Using Simple Hydroxamic Acid Derivatives Giglio, Benjamin C.; Schmidt, Valerie A.; Alexanian, Erik J. Journal of the American Chemical Society, Vol. 133, Issue 34 https://doi.org/10.1021/ja206306f	journal	August 2011
Mechanism of Copper(I)/TEMPO-Catalyzed Aerobic Alcohol Oxidation Hoover, Jessica M.; Ryland, Bradford L.; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 135, Issue 6 https://doi.org/10.1021/ja3117203	journal	January 2013
Combination of Redox-Active Ligand and Lewis Acid for Dioxygen Reduction with π-Bound Molybdenum−Quinonoid Complexes Henthorn, Justin T.; Lin, Sibo; Agapie, Theodor Journal of the American Chemical Society, Vol. 137, Issue 4 https://doi.org/10.1021/ja5100405	journal	January 2015
Dioxygen Activation by Mononuclear Nonheme Iron(II) Complexes Generates Iron−Oxygen Intermediates in the Presence of an NADH Analogue and Proton Hong, Seungwoo; Lee, Yong-Min; Shin, Woonsup Journal of the American Chemical Society, Vol. 131, Issue 39 https://doi.org/10.1021/ja905691f	journal	September 2009
Aerobic Oxidation of Primary Alcohols (Including Methanol) by Copper(II)− and Zinc(II)−Phenoxyl Radical Catalysts Chaudhuri, Phalguni; Hess, Martina; Müller, Jochen Journal of the American Chemical Society, Vol. 121, Issue 41 https://doi.org/10.1021/ja991481t	journal	October 1999
Generation and Oxidative Reactivity of a Ni(II) Superoxo Complex via Ligand-Based Redox Non-Innocence McNeece, Andrew J.; Jesse, Kate A.; Xie, Jiaze Journal of the American Chemical Society, Vol. 142, Issue 24 https://doi.org/10.1021/jacs.0c03244	journal	May 2020
Metal–Ligand Cooperation Facilitates Bond Activation and Catalytic Hydrogenation with Zinc Pincer Complexes Rauch, Michael; Kar, Sayan; Kumar, Amit Journal of the American Chemical Society, Vol. 142, Issue 34 https://doi.org/10.1021/jacs.0c05500	journal	July 2020
Direct Aerobic Generation of a Ferric Hydroperoxo Intermediate Via a Preorganized Secondary Coordination Sphere Jesse, Kate A.; Anferov, Sophie W.; Collins, Kelsey A. Journal of the American Chemical Society, Vol. 143, Issue 43 https://doi.org/10.1021/jacs.1c06911	journal	October 2021
Enzyme-Like Hydroxylation of Aliphatic C–H Bonds From an Isolable Co-Oxo Complex Goetz, McKenna K.; Schneider, Joseph E.; Filatov, Alexander S. Journal of the American Chemical Society, Vol. 143, Issue 49 https://doi.org/10.1021/jacs.1c09280	journal	December 2021
Chemical and Electrochemical O₂ Reduction on Earth-Abundant M-N-C Catalysts and Implications for Mediated Electrolysis Bates, Jason S.; Biswas, Sourav; Suh, Sung-Eun Journal of the American Chemical Society, Vol. 144, Issue 2 https://doi.org/10.1021/jacs.1c11126	journal	January 2022
Electrocatalytic Semihydrogenation of Terminal Alkynes Using Ligand-Based Transfer of Protons and Electrons Czaikowski, Maia E.; Anferov, Sophie W.; Tascher, Alex P. Journal of the American Chemical Society, Vol. 146, Issue 1 https://doi.org/10.1021/jacs.3c09885	journal	January 2024
Dioxygen Reduction by a Pd(0)–Hydroquinone Diphosphine Complex Horak, Kyle T.; Agapie, Theodor Journal of the American Chemical Society, Vol. 138, Issue 10 https://doi.org/10.1021/jacs.5b12928	journal	March 2016
Co(salophen)-Catalyzed Aerobic Oxidation of p -Hydroquinone: Mechanism and Implications for Aerobic Oxidation Catalysis Anson, Colin W.; Ghosh, Soumya; Hammes-Schiffer, Sharon Journal of the American Chemical Society, Vol. 138, Issue 12 https://doi.org/10.1021/jacs.6b00254	journal	March 2016
Reactivity of an Fe ^IV -Oxo Complex with Protons and Oxidants Hill, Ethan A.; Weitz, Andrew C.; Onderko, Elizabeth Journal of the American Chemical Society, Vol. 138, Issue 40 https://doi.org/10.1021/jacs.6b07633	journal	September 2016
The Ferraquinone–Ferrahydroquinone Couple: Combining Quinonic and Metal-Based Reactivity Dauth, Alexander; Gellrich, Urs; Diskin-Posner, Yael Journal of the American Chemical Society, Vol. 139, Issue 7 https://doi.org/10.1021/jacs.6b13050	journal	February 2017
Catalytic Synthesis of N-Heterocycles via Direct C(sp ³ )–H Amination Using an Air-Stable Iron(III) Species with a Redox-Active Ligand Bagh, Bidraha; Broere, Daniël L. J.; Sinha, Vivek Journal of the American Chemical Society, Vol. 139, Issue 14 https://doi.org/10.1021/jacs.7b00270	journal	March 2017
Electronic Structural Analysis of Copper(II)–TEMPO/ABNO Complexes Provides Evidence for Copper(I)–Oxoammonium Character Walroth, Richard C.; Miles, Kelsey C.; Lukens, James T. Journal of the American Chemical Society, Vol. 139, Issue 38 https://doi.org/10.1021/jacs.7b07186	journal	September 2017
Cooperative Electrocatalytic O ₂ Reduction Involving Co(salophen) with p- Hydroquinone as an Electron–Proton Transfer Mediator Anson, Colin W.; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 139, Issue 51 https://doi.org/10.1021/jacs.7b11362	journal	December 2017
Hydrogen Bonds Dictate O ₂ Capture and Release within a Zinc Tripod Dahl, Eric W.; Kiernicki, John J.; Zeller, Matthias Journal of the American Chemical Society, Vol. 140, Issue 32 https://doi.org/10.1021/jacs.8b04266	journal	July 2018
Catalytic Aerobic Oxidation of Alcohols by Copper Complexes Bearing Redox-Active Ligands with Tunable H-Bonding Groups Rajabimoghadam, Khashayar; Darwish, Yousef; Bashir, Umyeena Journal of the American Chemical Society, Vol. 140, Issue 48 https://doi.org/10.1021/jacs.8b08748	journal	November 2018
Tuning the Geometric and Electronic Structure of Synthetic High-Valent Heme Iron(IV)-Oxo Models in the Presence of a Lewis Acid and Various Axial Ligands Ehudin, Melanie A.; Gee, Leland B.; Sabuncu, Sinan Journal of the American Chemical Society, Vol. 141, Issue 14 https://doi.org/10.1021/jacs.9b00795	journal	March 2019
Radical Rebound Hydroxylation Versus H-Atom Transfer in Non-Heme Iron(III)-Hydroxo Complexes: Reactivity and Structural Differentiation Drummond, Michael J.; Ford, Courtney L.; Gray, Danielle L. Journal of the American Chemical Society, Vol. 141, Issue 16 https://doi.org/10.1021/jacs.9b01516	journal	April 2019
Mechanism of Catalytic O ₂ Reduction by Iron Tetraphenylporphyrin Pegis, Michael L.; Martin, Daniel J.; Wise, Catherine F. Journal of the American Chemical Society https://doi.org/10.1021/jacs.9b02640	journal	May 2019
Enabling Two-Electron Pathways with Iron and Cobalt: From Ligand Design to Catalytic Applications Arevalo, Rebeca; Chirik, Paul J. Journal of the American Chemical Society, Vol. 141, Issue 23 https://doi.org/10.1021/jacs.9b03337	journal	May 2019
Efficient and Practical Catalytic Oxidation of Alcohols Using Molecular Oxygen Markó, István E.; Gautier, Arnaud; Chellé-Regnaut, Isabelle The Journal of Organic Chemistry, Vol. 63, Issue 22 https://doi.org/10.1021/jo980770h	journal	October 1998
Metal−Ligand Cooperativity in O ₂ Activation: Observation of a “Pt−O−O−C” Peroxo Intermediate ^§ Scheuermann, Margaret L.; Fekl, Ulrich; Kaminsky, Werner Organometallics, Vol. 29, Issue 21 https://doi.org/10.1021/om1003946	journal	November 2010
Reactions of Five-Coordinate Platinum(IV) Complexes with Molecular Oxygen Scheuermann, Margaret L.; Luedtke, Avery T.; Hanson, Susan K. Organometallics, Vol. 32, Issue 17 https://doi.org/10.1021/om4003363	journal	August 2013
Iron Complexes Bearing Diphosphine Ligands with Positioned Pendant Amines as Electrocatalysts for the Oxidation of H ₂ Liu, Tianbiao; Liao, Qian; O’Hagan, Molly Organometallics, Vol. 34, Issue 12 https://doi.org/10.1021/om501289f	journal	May 2015
Superoxide dismutase activity enabled by a redox-active ligand rather than metal Ward, Meghan B.; Scheitler, Andreas; Yu, Meng Nature Chemistry, Vol. 10, Issue 12 https://doi.org/10.1038/s41557-018-0137-1	journal	October 2018
Redox-active ligands in catalysis Luca, Oana R.; Crabtree, Robert H. Chem. Soc. Rev., Vol. 42, Issue 4 https://doi.org/10.1039/C2CS35228A	journal	January 2013
Redox-induced fluoride ligand dissociation stabilized by intramolecular hydrogen bonding Moore, Cameron M.; Szymczak, Nathaniel K. Chemical Communications, Vol. 51, Issue 25 https://doi.org/10.1039/C4CC06832G	journal	January 2015
A pendant proton shuttle on [Fe ₄ N(CO) ₁₂ ] ⁻ alters product selectivity in formate vs. H ₂ production via the hydride [H–Fe ₄ N(CO) ₁₂ ] ⁻ Loewen, Natalia D.; Thompson, Emily J.; Kagan, Michael Chemical Science, Vol. 7, Issue 4 https://doi.org/10.1039/C5SC03169A	journal	January 2016
Detection of a transient Fe ^V (O)(OH) species involved in olefin oxidation by a bio-inspired non-haem iron catalyst Xu, Shuangning; Veach, Jedidiah J.; Oloo, Williamson N. Chemical Communications, Vol. 54, Issue 63 https://doi.org/10.1039/C8CC03990A	journal	January 2018
Insights into the dioxygen activation and catalytic mechanism of the nickel-containing quercetinase Li, Hong; Wang, Xiya; Tian, Ge Catalysis Science & Technology, Vol. 8, Issue 9 https://doi.org/10.1039/C8CY00187A	journal	January 2018
Influence of intramolecular secondary sphere hydrogen-bonding interactions on cytochrome c oxidase inspired low-spin heme–peroxo–copper complexes Ehudin, Melanie A.; Schaefer, Andrew W.; Adam, Suzanne M. Chemical Science, Vol. 10, Issue 10 https://doi.org/10.1039/C8SC05165H	journal	January 2019
Evaluation of attractive interactions in the second coordination sphere of iron complexes containing pendant amines Liao, Qian; Liu, Tianbiao; Johnson, Samantha I. Dalton Transactions, Vol. 48, Issue 15 https://doi.org/10.1039/C9DT00708C	journal	January 2019
Catalytic hydrogenation enabled by ligand-based storage of hydrogen McNeece, Andrew J.; Jesse, Kate A.; Filatov, Alexander S. Chemical Communications, Vol. 57, Issue 32 https://doi.org/10.1039/D0CC08236H	journal	January 2021
Cobalt complexes of redox noninnocent azo-aromatic pincers. Isolation, characterization, and application as catalysts for the synthesis of quinazolin-4(3 H )-ones Sinha, Suman; Das, Siuli; Mondal, Rakesh Dalton Transactions, Vol. 49, Issue 25 https://doi.org/10.1039/D0DT00394H	journal	January 2020
Non-covalent assembly of proton donors and p- benzoquinone anions for co-electrocatalytic reduction of dioxygen Hooe, Shelby L.; Cook, Emma N.; Reid, Amelia G. Chemical Science, Vol. 12, Issue 28 https://doi.org/10.1039/D1SC01271A	journal	January 2021
Evidence for the formation of a mononuclear ferric–hydroperoxo complex via the reaction of dioxygen with an (N4S(thiolate))iron(ii) complex Jiang, Yunbo; Telser, Joshua; Goldberg, David P. Chemical Communications, Issue 44 https://doi.org/10.1039/b913945a	journal	January 2009
Copper–O2 reactivity of tyrosinase models towards external monophenolic substrates: molecular mechanism and comparison with the enzyme Rolff, Malte; Schottenheim, Julia; Decker, Heinz Chemical Society Reviews, Vol. 40, Issue 7 https://doi.org/10.1039/c0cs00202j	journal	January 2011
Metal-free, aerobic ketooxygenation of alkenes using hydroxamic acids Schmidt, Valerie A.; Alexanian, Erik J. Chemical Science, Vol. 3, Issue 5 https://doi.org/10.1039/c2sc01042a	journal	January 2012
Nitroxide-catalyzed transition-metal-free aerobic oxidation processes Wertz, Sebastian; Studer, Armido Green Chemistry, Vol. 15, Issue 11 https://doi.org/10.1039/c3gc41459k	journal	January 2013
Disulfide reductive elimination from an iron(iii) complex Wong, Janice L.; Sánchez, Raúl Hernández; Logan, Jennifer Glancy Chemical Science, Vol. 4, Issue 4 https://doi.org/10.1039/c3sc22335c	journal	January 2013
Elucidation of the tyrosinase/O ₂ /monophenol ternary intermediate that dictates the monooxygenation mechanism in melanin biosynthesis Kipouros, Ioannis; Stańczak, Agnieszka; Ginsbach, Jake W. Proceedings of the National Academy of Sciences, Vol. 119, Issue 33 https://doi.org/10.1073/pnas.2205619119	journal	August 2022
Copper-Catalyzed Oxidation of Alcohols to Aldehydes and Ketones: An Efficient, Aerobic Alternative Marko, I. E.; Giles, P. R.; Tsukazaki, M. Science, Vol. 274, Issue 5295 https://doi.org/10.1126/science.274.5295.2044	journal	December 1996
Catalytic Galactose Oxidase Models: Biomimetic Cu(II)-Phenoxyl-Radical Reactivity Wang, Y. Science, Vol. 279, Issue 5350 https://doi.org/10.1126/science.279.5350.537	journal	January 1998
Isolating Fe-O2 Intermediates in Dioxygen Activation by Iron Porphyrin Complexes Lu, Xiaoyan; Wang, Shuang; Qin, Jian-Hua Molecules, Vol. 27, Issue 15 https://doi.org/10.3390/molecules27154690	journal	July 2022

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