Dual oxidase/oxygenase reactivity and resonance Raman spectra of {Cu3O2} moiety with perfluoro-t-butoxide ligands

Sarah E. N. Brazeau, Emily E. Norwine, Steven F. Hannigan, Nicole Orth, Ivana Ivanović-Burmazović, Dieter Rukser, Florian Biebl, Benjamin Grimm-Lebsanft, Gregor Praedel, Melissa Teubner, Michael Rübhausen, Patricia Liebhäuser, Thomas Rösener, Julia Stanek, Alexander Hoffmann, Sonja Herres-Pawlis and Linda H. Doerrer

Dalton Trans., 2019, 48, 6899
DOI: 10.1039/C9DT00516A

Hiking on the potential energy surface of a functional tyrosinase model – implications of singlet, broken-symmetry and triplet description

Alexander Hoffmann and Sonja Herres-Pawlis

Chem. Commun., 2014, 50, 403
DOI: 10.1039/C3CC46893C

Copper–O2 reactivity of tyrosinase models towards external monophenolic substrates: molecular mechanism and comparison with the enzyme

Malte Rolff, Julia Schottenheim, Heinz Decker and Felix Tuczek

Chem. Soc. Rev., 2011, 40, 4077
DOI: 10.1039/c0cs00202j

Synthetic models of the active site of catechol oxidase: mechanistic studies

Iryna A. Koval, Patrick Gamez, Catherine Belle, Katalin Selmeczi and Jan Reedijk

Chem. Soc. Rev., 2006, 35, 814
DOI: 10.1039/b516250p

Synthesis and crystal structures of a series of amide copper(II) complexes

El Houssine Alilou, Edith Amadei, Michel Giorgi, Marcel Pierrot and Marius Réglier

J. Chem. Soc., Dalton Trans., 1993, 549
DOI: 10.1039/DT9930000549

Cu(i)–O2 oxidation reactions in a fluorinated all-O-donor ligand environment

Sarah E. N. Brazeau and Linda H. Doerrer

Dalton Trans., 2019, 48, 4759
DOI: 10.1039/C8DT05028G

New catalytic model systems of tyrosinase: fine tuning of the reactivity with pyrazole-based N-donor ligands

Jessica Nadine Hamann and Felix Tuczek

Chem. Commun., 2014, 50, 2298
DOI: 10.1039/C3CC47888B

Copper monooxygenase models: hydroxylation reactions resulting from dioxygen activation by copper(I) complexes

Edith Amadéi, El Houssine Alilou, Franck Eydoux, Marcel Pierrot, Marius Réglier and Bernard Waegell

J. Chem. Soc., Chem. Commun., 1992, 1782
DOI: 10.1039/C39920001782

High-spin enforcement in first-row metal complexes of a constrained polyaromatic ligand: synthesis, structure, and properties

Lizhu Chen, Hunter A. Dulaney, Branford O. Wilkins, Sarah Farmer, Yanbing Zhang, Frank R. Fronczek and Jonah W. Jurss

New J. Chem., 2018, 42, 18667
DOI: 10.1039/C8NJ02072H

Copper–oxygen adducts: new trends in characterization and properties towards C–H activation

Jonathan De Tovar, Rébecca Leblay, Yongxing Wang, Laurianne Wojcik, Aurore Thibon-Pourret, Marius Réglier, A. Jalila Simaan, Nicolas Le Poul and Catherine Belle

Chem. Sci., 2024, 15, 10308
DOI: 10.1039/D4SC01762E

The bridge towards a more stable and active side-on-peroxido (Cu2II(µ-η2:η2-O2)) complex as a tyrosinase model system

Rosalie Dalhoff, Regina Schmidt, Lena Steeb, Kristina Rabatinova, Matthias Witte, Simon Teeuwen, Salim Benjamaâ, Henrika Hüppe, Alexander Hoffmann and Sonja Herres-Pawlis

Faraday Discuss., 2023, 244, 134
DOI: 10.1039/D2FD00162D

Copper-based redox shuttles supported by preorganized tetradentate ligands for dye-sensitized solar cells

Roberta R. Rodrigues, Joseph M. Lee, Natalie S. Taylor, Hammad Cheema, Lizhu Chen, Ryan C. Fortenberry, Jared H. Delcamp and Jonah W. Jurss

Dalton Trans., 2020, 49, 343
DOI: 10.1039/C9DT04030G

Copper-catalyzed divergent oxidative pathways of 2-naphthol derivatives: ortho-naphthoquinones versus 2-BINOLs

H. Y. Kim, S. Takizawa and K. Oh

Org. Biomol. Chem., 2016, 14, 7191
DOI: 10.1039/C6OB01183G

A bio-inspired synthesis of oxindoles by catalytic aerobic dual C–H functionalization of phenols

Zheng Huang, Mohammad S. Askari, Kenneth Virgel N. Esguerra, Tian-Yang Dai, Ohhyeon Kwon, Xavier Ottenwaelder and Jean-Philip Lumb

Chem. Sci., 2016, 7, 358
DOI: 10.1039/C5SC02395E

Catalytic aerobic oxidation of phenols to ortho-quinones with air-stable copper precatalysts

M. S. Askari, L. A. Rodríguez-Solano, A. Proppe, B. McAllister, J.-P. Lumb and X. Ottenwaelder

Dalton Trans., 2015, 44, 12094
DOI: 10.1039/C5DT00822K

Monooxygenation of an appended phenol in a model system of tyrosinase: implications on the enzymatic reaction mechanism

Jessica Nadine Hamann, Malte Rolff and Felix Tuczek

Dalton Trans., 2015, 44, 3251
DOI: 10.1039/C4DT03010A

Catecholase activity of dinuclear copper(II) complexes with variable endogenous and exogenous bridge

Jhumpa Mukherjee and Rabindranath Mukherjee

Inorganica Chimica Acta, 2002, 337, 429
DOI: 10.1016/S0020-1693(02)01106-4

Generation and Reactivity of μ-1,2-Peroxo CuIICuII and Bis-μ-oxo CuIIICuIII Species and Catalytic Hydroxylation of Benzene to Phenol with Hydrogen Peroxide

Lena Siebe, Christoph Butenuth, Anja Stammler, Hartmut Bögge, Stephan Walleck and Thorsten Glaser

Inorg. Chem., 2024, 63, 2627
DOI: 10.1021/acs.inorgchem.3c03914

Dioxygen activation by copper sites: relative stability and reactivity of (μ-η2:η2-peroxo)- and bis(μ-oxo)dicopper cores

Patrick L. Holland and William B. Tolman

Coordination Chemistry Reviews, 1999, 190-192, 855
DOI: 10.1016/S0010-8545(99)00125-3

Reactivity of Copper(I) Complexes Towards Dioxygen

Siegfried Schindler

Eur. J. Inorg. Chem., 2000, 2000, 2311
DOI: 10.1002/1099-0682(200011)2000:11<2311::AID-EJIC2311>3.0.CO;2-7

Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations

Rachel Trammell, Khashayar Rajabimoghadam and Isaac Garcia-Bosch

Chem. Rev., 2019, 119, 2954
DOI: 10.1021/acs.chemrev.8b00368

Kupfer‐katalysierte Monooxygenierung von Phenolen: Evidenz für einen mononuklearen Reaktionsmechanismus

Rebecca Schneider, Tobias A. Engesser, Christian Näther, Ingo Krossing and Felix Tuczek

Angewandte Chemie, 2022, 134
DOI: 10.1002/ange.202202562

Modeling Tyrosinase Monooxygenase Activity. Spectroscopic and Magnetic Investigations of Products Due to Reactions between Copper(I) Complexes of Xylyl-Based Dinucleating Ligands and Dioxygen: Aromatic Ring Hydroxylation and Irreversible Oxidation Products

Debalina Ghosh and Rabindranath Mukherjee

Inorg. Chem., 1998, 37, 6597
DOI: 10.1021/ic9713689

Selective Catalytic Oxidation of CH Bonds with Molecular Oxygen

Emil Roduner, Wolfgang Kaim, Biprajit Sarkar, Vlada B. Urlacher, Jürgen Pleiss, Roger Gläser, Wolf‐Dietrich Einicke, Georg A. Sprenger, Uwe Beifuß, Elias Klemm, Christian Liebner, Hartmut Hieronymus, Shih‐Fan Hsu, Bernd Plietker and Sabine Laschat

ChemCatChem, 2013, 5, 82
DOI: 10.1002/cctc.201200266

Influence of a Metal Substrate on Small‐Molecule Activation Mediated by a Surface‐Adsorbed Complex

Alexander Schlimm, Nadja Stucke, Benedikt M. Flöser, Talina Rusch, Jan Krahmer, Christian Näther, Thomas Strunskus, Olaf M. Magnussen and Felix Tuczek

Chemistry A European J, 2018, 24, 10732
DOI: 10.1002/chem.201800911

Monooxygenation of external phenolic substrates in small-molecule dicopper complexes: implications on the reaction mechanism of tyrosinase

Malte Rolff, Julia Schottenheim and Felix Tuczek

Journal of Coordination Chemistry, 2010, 63, 2382
DOI: 10.1080/00958972.2010.503273

Novel tert-Butyl Migration in Copper-Mediated Phenol Ortho-Oxygenation Implicates a Mechanism Involving Conversion of a 6-Hydroperoxy-2,4-cyclohexadienone Directly to an o-Quinone

Subrata Mandal, Dainius Macikenas, John D. Protasiewicz and Lawrence M. Sayre

J. Org. Chem., 2000, 65, 4804
DOI: 10.1021/jo991625m

Katalytische Phenolhydroxylierung mit Sauerstoff: Substratvielfalt jenseits der Proteinmatrix von Tyrosinase

Alexander Hoffmann, Cooper Citek, Stephan Binder, Arne Goos, Michael Rübhausen, Oliver Troeppner, Ivana Ivanović‐Burmazović, Erik C. Wasinger, T. Daniel P. Stack and Sonja Herres‐Pawlis

Angewandte Chemie, 2013, 125, 5508
DOI: 10.1002/ange.201301249

Low Temperature Syntheses and Reactivity of Cu2O2 Active-Site Models

Cooper Citek, Sonja Herres-Pawlis and T. Daniel P. Stack

Acc. Chem. Res., 2015, 48, 2424
DOI: 10.1021/acs.accounts.5b00220

Aerobic Copper-Catalyzed Organic Reactions

Scott E. Allen, Ryan R. Walvoord, Rosaura Padilla-Salinas and Marisa C. Kozlowski

Chem. Rev., 2013, 113, 6234
DOI: 10.1021/cr300527g

Theoretical Studies on ortho‐Oxidation of Phenols with Dioxygen Mediated by Dicopper Complex: Hints for a Catalyst with the Phenolase Activity of Tyrosinase

Hiroshi Naka, Yoshinori Kondo, Shinya Usui, Yuichi Hashimoto and Masanobu Uchiyama

Adv Synth Catal, 2007, 349, 595
DOI: 10.1002/adsc.200600557

Copper-catalyzed ortho-oxidation of phenols by dioxygen (tyrosinase mimics) do yields catechols as primary products

M. Maumy and P. Capdevielle

Journal of Molecular Catalysis A: Chemical, 1996, 113, 159
DOI: 10.1016/S1381-1169(96)00163-X

Catalytic Conversion of Monophenols to Ortho‐Quinones in a Tyrosinase‐Like Fashion: Towards More Biomimetic and More Efficient Model Systems

Julia Schottenheim, Natalie Fateeva, Wulf Thimm, Jan Krahmer and Felix Tuczek

Zeitschrift anorg allge chemie, 2013, 639, 1491
DOI: 10.1002/zaac.201300065

A novel monooxygenase model compound: the oxidative demethylation of a macrocyclic bicopper(I) complex

Cheng-Yu Shen, Ming-Fei Hu, Qin-Hui Luo and Meng-Chang Shen

Transition Met Chem, 1995, 20, 634
DOI: 10.1007/BF00136432

Exceptional Substrate Diversity in Oxygenation Reactions Catalyzed by a Bis(μ‐oxo) Copper Complex

Melanie Paul, Melissa Teubner, Benjamin Grimm‐Lebsanft, Christiane Golchert, Yannick Meiners, Laura Senft, Kristina Keisers, Patricia Liebhäuser, Thomas Rösener, Florian Biebl, Sören Buchenau, Maria Naumova, Vadim Murzin, Roxanne Krug, Alexander Hoffmann, Jörg Pietruszka, Ivana Ivanović‐Burmazović, Michael Rübhausen and Sonja Herres‐Pawlis

Chemistry A European J, 2020, 26, 7556
DOI: 10.1002/chem.202000664

Access to a CuII–O–CuII Motif: Spectroscopic Properties, Solution Structure, and Reactivity

Peter Haack, Anne Kärgel, Claudio Greco, Jadranka Dokic, Beatrice Braun, Florian F. Pfaff, Stefan Mebs, Kallol Ray and Christian Limberg

J. Am. Chem. Soc., 2013, 135, 16148
DOI: 10.1021/ja406721a

Dinucleating N‐donor Ligands with 1,2‐Diethynylbenzene Backbone for the Copper‐Mediated Monooxygenation of Phenols

Alexander Koch, Benjamin Herzigkeit, Küpra Yildiz, Christian Näther, Tobias A. Engesser and Felix Tuczek

Zeitschrift anorg allge chemie, 2024, 650
DOI: 10.1002/zaac.202300237

Molecular Structural Motifs and O2 Activation Inspired by Enzymes and Solid Catalysts

Stefan Yelin and Christian Limberg

Catal Lett, 2020, 150, 1
DOI: 10.1007/s10562-019-02918-0

Chiral Tripodal Ligand Containing Three N-Heterocyclic Donor Functions and Its Copper Complexes: Crystallization of [LCuI]22+/[L2CuII]2+ Stereoisomers and Tyrosinase Activity

Aline Arnold, Christian Limberg and Ramona Metzinger

Inorg. Chem., 2012, 51, 12210
DOI: 10.1021/ic301391s

A novel catalytic system for oxygenation with molecular oxygen induced by transition metal complexes with a multidentate N-heterocyclic podand ligand

Toshikazu Hirao, Toshiyuki Moriuchi, Takuji Ishikawa, Kouichirou Nishimura, Satoshi Mikami, Yoshiki Ohshiro and Isao Ikeda

Journal of Molecular Catalysis A: Chemical, 1996, 113, 117
DOI: 10.1016/S1381-1169(96)00052-0

Catalytic Models of Tyrosinase: Reactivity Differences between Systems Based on Mono‐ and Binucleating Ligands

Julia Schottenheim, Claus Gernert, Benjamin Herzigkeit, Jan Krahmer and Felix Tuczek

Eur J Inorg Chem, 2015, 2015, 3501
DOI: 10.1002/ejic.201500029

Employing Linear Tridentate Ligands with Pyrazole End Groups in Catalytic Tyrosinase Model Chemistry: Does Hemilability Matter?

Benjamin Herzigkeit, Ramona Jurgeleit, Benedikt M. Flöser, Nadja E. Meißner, Tobias A. Engesser, Christian Näther and Felix Tuczek

Eur J Inorg Chem, 2019, 2019, 2258
DOI: 10.1002/ejic.201900242

Stoichiometric and catalytic oxidation by a dinuclear copper(I) dioxygen complex and a dinuclear cpper(II) complex of a macrocyclic ligand derived from the 2:2 condensation of pyridine-2,6-dicarboxaldehyde and 1,4,7-triazaheptane

David A. Rockcliffe and Arthur E. Martell

Journal of Molecular Catalysis A: Chemical, 1995, 99, 101
DOI: 10.1016/1381-1169(95)00033-X

Structural and Reactivity Models for Copper Oxygenases: Cooperative Effects and Novel Reactivities

Joan Serrano-Plana, Isaac Garcia-Bosch, Anna Company and Miquel Costas

Acc. Chem. Res., 2015, 48, 2397
DOI: 10.1021/acs.accounts.5b00187

Catalytic Phenol Hydroxylation with Dioxygen: Extension of the Tyrosinase Mechanism beyond the Protein Matrix

Alexander Hoffmann, Cooper Citek, Stephan Binder, Arne Goos, Michael Rübhausen, Oliver Troeppner, Ivana Ivanović‐Burmazović, Erik C. Wasinger, T. Daniel P. Stack and Sonja Herres‐Pawlis

Angew Chem Int Ed, 2013, 52, 5398
DOI: 10.1002/anie.201301249

Biomimetic Hydroxylation Catalysis Through Self‐Assembly of a Bis(pyrazolyl)methane Copper–Peroxo Complex

Claudia Wilfer, Patricia Liebhäuser, Hannes Erdmann, Alexander Hoffmann and Sonja Herres‐Pawlis

Eur J Inorg Chem, 2015, 2015, 494
DOI: 10.1002/ejic.201402957

Dinuclear Copper Complex with a Pyridazine‐Bridged Octadentate Ligand: Monooxygenase Activity and Characterization of Copper‐Oxygen Intermediates

Alexander Stüber, Ramona Jurgeleit, Benjamin Grimm‐Lebsanft, Sören Buchenau, Ina Kellner, Yannik Appiarius, Christian Näther, Jan Krahmer, Ivana Ivanović‐Burmazović, Michael Rübhausen, Maria A. Naumova and Felix Tuczek

Chemistry A European J, 2025, 31
DOI: 10.1002/chem.202501659

Synthesis, structural characterization and dioxygen reactivity of imidazole-ligated Cu(I) complexes

Thomas N. Sorrell, Martha L. Garrity, Joseph L. Richards and Peter S. White

Inorganica Chimica Acta, 1994, 218, 103
DOI: 10.1016/0020-1693(93)03792-9

Bioinspired Copper(I) Complexes that Exhibit Monooxygenase and Catechol Dioxygenase Activity

Aline Arnold, Ramona Metzinger and Christian Limberg

Chemistry A European J, 2015, 21, 1198
DOI: 10.1002/chem.201405155

Catalytic Oxygenation of Hydrocarbons by Mono‐μ‐oxo Dicopper(II) Species Resulting from O−O Cleavage of Tetranuclear CuI/CuII Peroxo Complexes

Ramona Jurgeleit, Benjamin Grimm‐Lebsanft, Benedikt Maria Flöser, Melissa Teubner, Sören Buchenau, Laura Senft, Jonas Hoffmann, Maria Naumova, Christian Näther, Ivana Ivanović‐Burmazović, Michael Rübhausen and Felix Tuczek

Angew Chem Int Ed, 2021, 60, 14154
DOI: 10.1002/anie.202101035

Tuning the Activity of Catechol Oxidase Model Complexes by Geometric Changes of the Dicopper Core

Jens Ackermann, Franc Meyer, Elisabeth Kaifer and Hans Pritzkow

Chem. Eur. J., 2002, 8, 247
DOI: 10.1002/1521-3765(20020104)8:1<247::AID-CHEM247>3.0.CO;2-P

Activation of C−H Bonds by Metal Complexes

Alexander E. Shilov and Georgiy B. Shul'pin

Chem. Rev., 1997, 97, 2879
DOI: 10.1021/cr9411886

Binding of 2-Hydroxypyridine-N-oxide on Dicopper(II) Centers: Insights into Tyrosinase Inhibition Mechanism by Transition-State Analogs

Eugénie Peyroux, Wadih Ghattas, Renaud Hardré, Michel Giorgi, Bruno Faure, A. Jalila Simaan, Catherine Belle and Marius Réglier

Inorg. Chem., 2009, 48, 10874
DOI: 10.1021/ic901593x

Building biomimetic model compounds of dinuclear and trinuclear copper clusters for stereoselective oxidations

Eliana Lo Presti, Enrico Monzani, Laura Santagostini and Luigi Casella

Inorganica Chimica Acta, 2018, 481, 47
DOI: 10.1016/j.ica.2017.09.045

Catalytic epoxidation of unfunctionalized alkenes by dinuclear nickel(II) complexes

Minze T. Rispens, Onko Jan Gelling, AndréH.M. de Vries, Auke Meetsma, Fré van Bolhuis and Ben L. Feringa

Tetrahedron, 1996, 52, 3521
DOI: 10.1016/0040-4020(96)00030-0

Oligodentate Aminotriazole Ligands for CuAAC and Copper‐Mediated Monooxygenation of Phenols: Influence of Denticity, Chain Length and N‐Alkylation on Catalytic Activity

Alexander Koch, Tobias A. Engesser, C. Näther and Felix Tuczek

ChemCatChem, 2024, 16
DOI: 10.1002/cctc.202301316

Molecular CuII‐O‐CuIIComplexes: Still Waters Run Deep

Peter Haack and Christian Limberg

Angew Chem Int Ed, 2014, 53, 4282
DOI: 10.1002/anie.201309505

Click. Coordinate. Catalyze. Using CuAAC Click Ligands in Small‐Molecule Model Chemistry of Tyrosinase

Benjamin Herzigkeit, Benedikt M. Flöser, Nadja E. Meißner, Tobias A. Engesser and Felix Tuczek

ChemCatChem, 2018, 10, 5402
DOI: 10.1002/cctc.201801606

Copper Complexes Supported by Iminotriazole Ligands: Effective Catalysts for the Monooxygenation of Phenols

Alexander Koch, Tobias A. Engesser and Felix Tuczek

Organometallics, 2023, 42, 1774
DOI: 10.1021/acs.organomet.3c00014

Oxygen insertion in organic substrates catalyzed by copper compounds

E. Spodine and J. Manzur

Coordination Chemistry Reviews, 1992, 119, 171
DOI: 10.1016/0010-8545(92)80033-N

Molekulare CuII‐O‐CuII‐Komplexe: Stille Wasser sind tief

Peter Haack and Christian Limberg

Angewandte Chemie, 2014, 126, 4368
DOI: 10.1002/ange.201309505

Dinuclear Copper(I) Complexes Supported by Bis‐Tridentate N‐Donor‐Ligands: Turning‐On Tyrosinase Activity

Rebecca Schneider, Tobias A. Engesser, Jessica N. Hamann, Christian Näther and Felix Tuczek

Eur J Inorg Chem, 2022, 2022
DOI: 10.1002/ejic.202200509

Designer Ligands. Part 5.1Synthesis of Polydentate Biphenyl Ligands

Stephanie G. Burton, Perry T. Kay and Kevin Wellington

Synthetic Communications, 2000, 30, 511
DOI: 10.1080/00397910008087347

High-valent copper in biomimetic and biological oxidations

William Keown, J. Brannon Gary and T. Daniel P. Stack

J Biol Inorg Chem, 2017, 22, 289
DOI: 10.1007/s00775-016-1420-5

4. Copper

Brian P. Murphy

Coordination Chemistry Reviews, 1993, 124, 63
DOI: 10.1016/0010-8545(93)80005-P

Crystal structures and energy refinement of some 2,2′-disubstituted biphenyl compounds

L. Benmenni, E. H. Alilou, M. Giorgi, M. Pierrot and M. Réglier

J Chem Crystallogr, 1994, 24, 345
DOI: 10.1007/BF01670212

A Biomimetic Catalytic Aerobic Functionalization of Phenols

Kenneth Virgel N. Esguerra, Yacoub Fall and Jean‐Philip Lumb

Angewandte Chemie, 2014, 126, 5987
DOI: 10.1002/ange.201311103

Tyrosinase-catecholic substrates in Vitro model: kinetic studies on the o-quinone/o-semiquinone radical formation

Rosa Pia Ferrari, Enzo Laurenti, Elena Maria Ghibaudi and Luigi Casella

Journal of Inorganic Biochemistry, 1997, 68, 61
DOI: 10.1016/S0162-0134(97)81617-0

From Phenols to Antimicrobial Phenazines: Tyrosinase‐like Catalytic Activity of a Bisguanidine Based Bis(μ‐oxido) Complex

Larissa Laurini, Salvatore Marco Conte, Karl Hüser, Paul R. F. Cordero, Heliana Michaela Núñez Ponce, Stefanie Zimmer, Lars Lauterbach and Sonja Herres‐Pawlis

Eur J Inorg Chem, 2024, 27
DOI: 10.1002/ejic.202300700

Selective Aromatic Hydroxylation with Dioxygen and Simple Copper Imine Complexes

Jonathan Becker, Puneet Gupta, Friedrich Angersbach, Felix Tuczek, Christian Näther, Max C. Holthausen and Siegfried Schindler

Chemistry A European J, 2015, 21, 11735
DOI: 10.1002/chem.201501003

Synthesis, crystal structure, spectral and magnetic studies and catecholase activity of copper(II) complexes with di- and tri-podal ligands

Vimal K. Bhardwaj, Núria Aliaga-Alcalde, Montserrat Corbella and Geeta Hundal

Inorganica Chimica Acta, 2010, 363, 97
DOI: 10.1016/j.ica.2009.09.041

Formation of Hybrid Guanidine‐Stabilized Bis(μ‐oxo)dicopper Cores in Solution: Electronic and Steric Perturbations

Sonja Herres‐Pawlis, Roxana Haase, Pratik Verma, Alexander Hoffmann, Peng Kang and T. Daniel P. Stack

Eur J Inorg Chem, 2015, 2015, 5426
DOI: 10.1002/ejic.201500884

Functional Modeling of Tyrosinase. Mechanism of Phenolortho-Hydroxylation by Dinuclear Copper Complexes

Luigi Casella, Enrico Monzani, Michele Gullotti, Daniela Cavagnino, Gianluca Cerina, Laura Santagostini and Renato Ugo

Inorg. Chem., 1996, 35, 7516
DOI: 10.1021/ic9601100

Heterogenized polymetallic catalysts Part II. Oxidation of 3,5-di-t-butylphenol by Cu(II), Fe(III) and Pd(II) complexed to a polyphenylene polymer containing ß-di- and triketone surface ligands; an improved catalyst system

Patrick M. Henry, Xiaoli Ma, Glenn Noronha and Kyaw Zaw

Inorganica Chimica Acta, 1995, 240, 205
DOI: 10.1016/0020-1693(95)04536-8

Synthesis, characterization, and tyrosinase biomimetic catalytic activity of copper(II) complexes with schiff base ligands derived from α-diketones with 2-methyl-3-amino-(3H)-quinazolin-4-one

Abd El-Motaleb M. Ramadan, Mohamed M. Ibrahim and Shaban Y. Shaban

Journal of Molecular Structure, 2011, 1006, 348
DOI: 10.1016/j.molstruc.2011.09.031

Synthesis and Catalytic Reactivity of a Dicopper(II) μ-η2:η2-Peroxo Species Supported by 1,4,7-Tri-tert-butyl-1,4,7-triazacyclononane

Gregory J. Karahalis, Arumugam Thangavel, Bryant Chica, John Bacsa, R. Brian Dyer and Christopher C. Scarborough

Inorg. Chem., 2016, 55, 1102
DOI: 10.1021/acs.inorgchem.5b02205

Molecular structure and catechol oxidase activity of a new copper(I) complex with sterically crowded monodentate N-donor ligand

Ádám Kupán, József Kaizer, Gábor Speier, Michel Giorgi, Marius Réglier and Ferenc Pollreisz

Journal of Inorganic Biochemistry, 2009, 103, 389
DOI: 10.1016/j.jinorgbio.2008.11.015

Theoretical study of oxyhemocyanin active site: A possible insight on the first step of phenol oxidation by tyrosinase

O. Eisenstein, C. Giessner-Prettre, J. Maddaluno, D. Stussi and J. Weber

Archives of Biochemistry and Biophysics, 1992, 296, 247
DOI: 10.1016/0003-9861(92)90569-I

Small-molecule models of tyrosinase: From ligand hydroxylation to catalytic monooxygenation of external substrates

Jessica Nadine Hamann, Benjamin Herzigkeit, Ramona Jurgeleit and Felix Tuczek

Coordination Chemistry Reviews, 2017, 334, 54
DOI: 10.1016/j.ccr.2016.07.009

Room temperature stable multitalent: highly reactive and versatile copper guanidine complexes in oxygenation reactions

Melanie Paul, Alexander Hoffmann and Sonja Herres-Pawlis

J Biol Inorg Chem, 2021, 26, 249
DOI: 10.1007/s00775-021-01849-9

A Biomimetic Catalytic Aerobic Functionalization of Phenols

Kenneth Virgel N. Esguerra, Yacoub Fall and Jean‐Philip Lumb

Angew Chem Int Ed, 2014, 53, 5877
DOI: 10.1002/anie.201311103

A Biomimetic Mechanism for the Copper-Catalyzed Aerobic Oxygenation of 4-tert-Butylphenol

Mohammad S. Askari, Kenneth Virgel N. Esguerra, Jean-Philip Lumb and Xavier Ottenwaelder

Inorg. Chem., 2015, 54, 8665
DOI: 10.1021/acs.inorgchem.5b01297

Structural and functional models for the dinuclear copper active site in catechol oxidases

Marta González-Álvarez, Gloria Alzuet, Joaquı́n Borrás, Santiago Garcı́a-Granda and José Manuel Montejo-Bernardo

Journal of Inorganic Biochemistry, 2003, 96, 443
DOI: 10.1016/S0162-0134(03)00263-0

Catalytic aerobic oxidation of halogenated phenols

Kenneth Virgel N. Esguerra, Yacoub Fall and Jean-Philip Lumb

Inorganica Chimica Acta, 2018, 481, 197
DOI: 10.1016/j.ica.2017.08.009

Tyrosinase and catechol oxidase activity of copper(I) complexes supported by imidazole-based ligands: structure–reactivity correlations

Franziska Wendt, Christian Näther and Felix Tuczek

J Biol Inorg Chem, 2016, 21, 777
DOI: 10.1007/s00775-016-1370-y

Crystal structure, spectral and magnetic properties of a new (μ-acetate) (μ-alkoxide) dicopper (II) complex as a model for tyrosinase

Ademir Neves, Liane M. Rossi, Ivo Vencato, Valderes Drago, Wolfgang Haase and Rüdiger Werner

Inorganica Chimica Acta, 1998, 281, 111
DOI: 10.1016/S0020-1693(98)00142-X

Record Broken: A Copper Peroxide Complex with Enhanced Stability and Faster Hydroxylation Catalysis

Patricia Liebhäuser, Kristina Keisers, Alexander Hoffmann, Thomas Schnappinger, Isabella Sommer, Anne Thoma, Claudia Wilfer, Roland Schoch, Kai Stührenberg, Matthias Bauer, Maximilian Dürr, Ivana Ivanović‐Burmazović and Sonja Herres‐Pawlis

Chemistry A European J, 2017, 23, 12171
DOI: 10.1002/chem.201700887

A novel system for oxygenation. Effect of multidentate podand ligand in transition metal catalyzed epoxidation with molecular oxygen

Toshikazu Hirao, Toshiyuki Moriuchi, Satoshi Mikami, Isao Ikeda and Yoshiki Ohshiro

Tetrahedron Letters, 1993, 34, 1031
DOI: 10.1016/S0040-4039(00)77484-3

Controlling the Catalytic Aerobic Oxidation of Phenols

Kenneth Virgel N. Esguerra, Yacoub Fall, Laurène Petitjean and Jean-Philip Lumb

J. Am. Chem. Soc., 2014, 136, 7662
DOI: 10.1021/ja501789x

Tyrosinase Model Systems Supported by Pyrazolylmethylpyridine Ligands: Electronic and Steric Factors Influencing the Catalytic Activity and Impact of Complex Equilibria in Solution

Benjamin Herzigkeit, Benedikt M. Flöser, Tobias A. Engesser, Christian Näther and Felix Tuczek

Eur J Inorg Chem, 2018, 2018, 3058
DOI: 10.1002/ejic.201800319

Influence of the amine donor on hybrid guanidine-stabilized Bis(μ-oxido) dicopper(III) complexes and their tyrosinase-like oxygenation activity towards polycyclic aromatic alcohols

Melanie Paul, Melissa Teubner, Benjamin Grimm-Lebsanft, Sören Buchenau, Alexander Hoffmann, Michael Rübhausen and Sonja Herres-Pawlis

Journal of Inorganic Biochemistry, 2021, 224, 111541
DOI: 10.1016/j.jinorgbio.2021.111541

Katalytische Oxygenierung von Kohlenwasserstoffen durch Mono‐μ‐oxo‐Dikupfer(II)‐Spezies erzeugt durch O‐O‐Spaltung von tetranuklearen CuI/CuII‐Peroxo‐Komplexen

Ramona Jurgeleit, Benjamin Grimm‐Lebsanft, Benedikt Maria Flöser, Melissa Teubner, Sören Buchenau, Laura Senft, Jonas Hoffmann, Maria Naumova, Christian Näther, Ivana Ivanović‐Burmazović, Michael Rübhausen and Felix Tuczek

Angewandte Chemie, 2021, 133, 14273
DOI: 10.1002/ange.202101035

Copper‐Catalyzed Monooxygenation of Phenols: Evidence for a Mononuclear Reaction Mechanism

Rebecca Schneider, Tobias A. Engesser, Christian Näther, Ingo Krossing and Felix Tuczek

Angew Chem Int Ed, 2022, 61
DOI: 10.1002/anie.202202562

Das erste katalytische Tyrosinasemodell basierend auf einem einkernigen Kupfer(I)‐Komplex: Kinetik und Mechanismus

Malte Rolff, Julia Schottenheim, Gerhard Peters and Felix Tuczek

Angewandte Chemie, 2010, 122, 6583
DOI: 10.1002/ange.201000973

Zeolite-Y Encapsulated Metal Picolinato Complexes as Catalyst for Oxidation of Phenol with Hydrogen Peroxide

Kusum K. Bania and Ramesh C. Deka

J. Phys. Chem. C, 2013, 117, 11663
DOI: 10.1021/jp402439x

Stoichiometric and catalytic oxidations by dinuclear copper(I) and copper(II) complexes of a Schiff base ligand derived from the 2:2 condensation of pyridine 2,6-dicarboxaldehyde and 1,5,9-triazanonane

David A. Rockcliffe and Arthur E. Martell

Journal of Molecular Catalysis A: Chemical, 1996, 106, 211
DOI: 10.1016/1381-1169(95)00272-3

The First Catalytic Tyrosinase Model System Based on a Mononuclear Copper(I) Complex: Kinetics and Mechanism

Malte Rolff, Julia Schottenheim, Gerhard Peters and Felix Tuczek

Angew Chem Int Ed, 2010, 49, 6438
DOI: 10.1002/anie.201000973

Synthesis of new dinuclear dicopper(II) and dinickel(II) complexes. The kinetics of catechol oxidase and electrochemistry of a dicopper(II) complex

Farukh Arjmand, Shamima Parveen and Sartaj Tabassum

Transition Met Chem, 2005, 30, 128
DOI: 10.1007/s11243-004-1019-5

Molybdenum Complexes Supported by PN3P Pincer Ligands: Synthesis, Characterization, and Application to Synthetic Nitrogen Fixation

Nadja Stucke, Jan Krahmer, Christian Näther and Felix Tuczek

Eur J Inorg Chem, 2018, 2018, 5108
DOI: 10.1002/ejic.201801194

Homogeneous oxidative transformations mediated by copper catalyst systems

Lindie Marais, Hermanus C.M. Vosloo and Andrew J. Swarts

Coordination Chemistry Reviews, 2021, 440, 213958
DOI: 10.1016/j.ccr.2021.213958

Alkane Oxidation: Methane Monooxygenases, Related Enzymes, and Their Biomimetics

Vincent C.-C. Wang, Suman Maji, Peter P.-Y. Chen, Hung Kay Lee, Steve S.-F. Yu and Sunney I. Chan

Chem. Rev., 2017, 117, 8574
DOI: 10.1021/acs.chemrev.6b00624

Aerobic Aliphatic Hydroxylation Reactions by Copper Complexes: A Simple Clip‐and‐Cleave Concept

Jonathan Becker, Yevheniia Y. Zhyhadlo, Ekaterina D. Butova, Andrey A. Fokin, Peter R. Schreiner, Moritz Förster, Max C. Holthausen, Pascal Specht and Siegfried Schindler

Chemistry A European J, 2018, 24, 15543
DOI: 10.1002/chem.201802607

Catalytic Galactose Oxidase Models: Biomimetic Cu(II)-Phenoxyl-Radical Reactivity

Yadong Wang, Jennifer L. DuBois, Britt Hedman, Keith O. Hodgson and T. D. P. Stack

Science, 1998, 279, 537
DOI: 10.1126/science.279.5350.537

Modeling tyrosinase activity. Effect of ligand topology on aromatic ring hydroxylation: An overview

Anindita De, Sukanta Mandal and Rabindranath Mukherjee

Journal of Inorganic Biochemistry, 2008, 102, 1170
DOI: 10.1016/j.jinorgbio.2008.01.030

Earth-Abundant Mixed-Metal Catalysts for Hydrocarbon Oxygenation

James R. Pankhurst, Massimiliano Curcio, Stephen Sproules, Guy C. Lloyd-Jones and Jason B. Love

Inorg. Chem., 2018, 57, 5915
DOI: 10.1021/acs.inorgchem.8b00420

Catalytic oxygenation of various monophenols by copper(I) complexes with bis(pyrazolyl)methane ligands: differences in reactivity

Jessica Nadine Hamann, Rebecca Schneider and Felix Tuczek

Journal of Coordination Chemistry, 2015, 68, 3259
DOI: 10.1080/00958972.2015.1074191

Multidentate N-heterocyclic podand ligand. Efficient oxygenation of phenols catalyzed by novel cobalt complex

Toshiyuki Moriuchi, Toshikazu Hirao, Takuji Ishikawa, Yoshiki Ohshiro and Isao Ikeda

Journal of Molecular Catalysis A: Chemical, 1995, 95, L1
DOI: 10.1016/1381-1169(94)00164-2

Dinuclear Copper Complexes Based on Parallel β-Diiminato Binding Sites and their Reactions with O2: Evidence for a Cu−O−Cu Entity

Peter Haack, Christian Limberg, Kallol Ray, Beatrice Braun, Uwe Kuhlmann, Peter Hildebrandt and Christian Herwig

Inorg. Chem., 2011, 50, 2133
DOI: 10.1021/ic101249k

Reactivity of Copper(I) Complexes Containing Ligands Derived from (1S,3R)‐Camphoric Acid with Dioxygen

Fabian Stöhr, Niclas Kulhanek, Jonathan Becker, Richard Göttlich and Siegfried Schindler

Eur J Inorg Chem, 2021, 2021, 2079
DOI: 10.1002/ejic.202100187

Efficient Biomimetic Hydroxylation Catalysis with a Bis(pyrazolyl)imidazolylmethane Copper Peroxide Complex

Claudia Wilfer, Patricia Liebhäuser, Alexander Hoffmann, Hannes Erdmann, Oleg Grossmann, Leander Runtsch, Eva Paffenholz, Rahel Schepper, Regina Dick, Matthias Bauer, Maximilian Dürr, Ivana Ivanović‐Burmazović and Sonja Herres‐Pawlis

Chemistry A European J, 2015, 21, 17639
DOI: 10.1002/chem.201501685