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Literature DB >> 28103018

Copper-Oxygen Complexes Revisited: Structures, Spectroscopy, and Reactivity.

Courtney E Elwell¹, Nicole L Gagnon¹, Benjamin D Neisen¹, Debanjan Dhar¹, Andrew D Spaeth¹, Gereon M Yee¹, William B Tolman¹.

Abstract

A longstanding research goal has been to understand the nature and role of copper-oxygen intermediates within copper-containing enzymes and abiological catalysts. Synthetic chemistry has played a pivotal role in highlighting the viability of proposed intermediates and expanding the library of known copper-oxygen cores. In addition to the number of new complexes that have been synthesized since the previous reviews on this topic in this journal (Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Chem. Rev. 2004, 104, 1013-1046 and Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047-1076), the field has seen significant expansion in the (1) range of cores synthesized and characterized, (2) amount of mechanistic work performed, particularly in the area of organic substrate oxidation, and (3) use of computational methods for both the corroboration and prediction of proposed intermediates. The scope of this review has been limited to well-characterized examples of copper-oxygen species but seeks to provide a thorough picture of the spectroscopic characteristics and reactivity trends of the copper-oxygen cores discussed.

Entities: Chemical

Mesh：

Substances：
Copper
Oxygen

Year: 2017 PMID： 28103018 PMCID： PMC5963733 DOI： 10.1021/acs.chemrev.6b00636

Source DB: PubMed Journal: Chem Rev ISSN： 0009-2665 Impact factor: 60.622

305 in total

1. Sulfur donor atom effects on copper(I)/O(2) chemistry with thioanisole containing tetradentate N(3)S ligand leading to μ-1,2-peroxo-dicopper(II) species.

Authors: Yunho Lee; Dong-Heon Lee; Ga Young Park; Heather R Lucas; Amy A Narducci Sarjeant; Matthew T Kieber-Emmons; Michael A Vance; Ashley E Milligan; Edward I Solomon; Kenneth D Karlin
Journal: Inorg Chem Date: 2010-10-04 Impact factor: 5.165

2. Dioxygen activation at a single copper site: structure, bonding, and mechanism of formation of 1:1 Cu-O2 adducts.

Authors: Nermeen W Aboelella; Sergey V Kryatov; Benjamin F Gherman; William W Brennessel; Victor G Young; Ritimukta Sarangi; Elena V Rybak-Akimova; Keith O Hodgson; Britt Hedman; Edward I Solomon; Christopher J Cramer; William B Tolman
Journal: J Am Chem Soc Date: 2004-12-29 Impact factor: 15.419

3. Hydroxylation of phenolic compounds by a peroxodicopper(II) complex: further insight into the mechanism of tyrosinase.

Authors: Sara Palavicini; Alessandro Granata; Enrico Monzani; Luigi Casella
Journal: J Am Chem Soc Date: 2005-12-28 Impact factor: 15.419

4. Facile O-atom insertion into C-C and C-H bonds by a trinuclear copper complex designed to harness a singlet oxene.

Authors: Peter P-Y Chen; Richard B-G Yang; Jason C-M Lee; Sunney I Chan
Journal: Proc Natl Acad Sci U S A Date: 2007-09-05 Impact factor: 11.205

5. Enzymatic C-H activation by metal-superoxo intermediates.

Authors: J Martin Bollinger; Carsten Krebs
Journal: Curr Opin Chem Biol Date: 2007-03-19 Impact factor: 8.822

6. Investigation of the hydroxylation mechanism of noncoupled copper oxygenases by ab initio molecular dynamics simulations.

Authors: Conchín Meliá; Silvia Ferrer; Jan Řezáč; Olivier Parisel; Olivia Reinaud; Vicent Moliner; Aurélien de la Lande
Journal: Chemistry Date: 2013-11-20 Impact factor: 5.236

7. Evidence for Cu-O2 intermediates in superoxide oxidations by biomimetic copper(II) complexes.

Authors: Valeriy V Smirnov; Justine P Roth
Journal: J Am Chem Soc Date: 2006-03-22 Impact factor: 15.419

8. Heterobimetallic dioxygen activation: synthesis and reactivity of mixed Cu-Pd and Cu-Pt bis(mu-oxo) complexes.

Authors: John T York; Antoni Llobet; Christopher J Cramer; William B Tolman
Journal: J Am Chem Soc Date: 2007-06-06 Impact factor: 15.419

9. Effects of thioether substituents on the O2 reactivity of beta-diketiminate-Cu(I) complexes: probing the role of the methionine ligand in copper monooxygenases.

Authors: Nermeen W Aboelella; Benjamin F Gherman; Lyndal M R Hill; John T York; Nicole Holm; Victor G Young; Christopher J Cramer; William B Tolman
Journal: J Am Chem Soc Date: 2006-03-15 Impact factor: 15.419

10. Geometric and electronic structure of [{Cu(MeAN)}2(μ-η2:η2(O2(2-)))]2+ with an unusually long O-O bond: O-O bond weakening vs activation for reductive cleavage.

Authors: Ga Young Park; Munzarin F Qayyum; Julia Woertink; Keith O Hodgson; Britt Hedman; Amy A Narducci Sarjeant; Edward I Solomon; Kenneth D Karlin
Journal: J Am Chem Soc Date: 2012-05-09 Impact factor: 15.419

68 in total

1. Mechanisms for Hydrogen-Atom Abstraction by Mononuclear Copper(III) Cores: Hydrogen-Atom Transfer or Concerted Proton-Coupled Electron Transfer?

Authors: Mukunda Mandal; Courtney E Elwell; Caitlin J Bouchey; Timothy J Zerk; William B Tolman; Christopher J Cramer
Journal: J Am Chem Soc Date: 2019-10-16 Impact factor: 15.419

2. Intramolecular Hydrogen Bonding Enhances Stability and Reactivity of Mononuclear Cupric Superoxide Complexes.

Authors: Mayukh Bhadra; Jung Yoon C Lee; Ryan E Cowley; Sunghee Kim; Maxime A Siegler; Edward I Solomon; Kenneth D Karlin
Journal: J Am Chem Soc Date: 2018-07-13 Impact factor: 15.419

3. Exclusive imidazole ligation to Cu^III₂O₂ and Cu^IIICu^II₂O₂ cores.

Authors: William Keown; Tao A G Large; Linus Chiang; Erik C Wasinger; T Daniel P Stack
Journal: Chem Commun (Camb) Date: 2019-06-20 Impact factor: 6.222

Review 4. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

Authors: Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal: Chem Rev Date: 2019-01-30 Impact factor: 60.622

5. Determination of the Cu(III)-OH Bond Distance by Resonance Raman Spectroscopy Using a Normalized Version of Badger's Rule.

Authors: Andrew D Spaeth; Nicole L Gagnon; Debanjan Dhar; Gereon M Yee; William B Tolman
Journal: J Am Chem Soc Date: 2017-03-20 Impact factor: 15.419

6. Impact of Intramolecular Hydrogen Bonding on the Reactivity of Cupric Superoxide Complexes with O-H and C-H Substrates.

Authors: Daniel E Diaz; David A Quist; Austin E Herzog; Andrew W Schaefer; Ioannis Kipouros; Mayukh Bhadra; Edward I Solomon; Kenneth D Karlin
Journal: Angew Chem Int Ed Engl Date: 2019-10-23 Impact factor: 15.336

Copper-Oxygen Complexes Revisited: Structures, Spectroscopy, and Reactivity.

1. Sulfur donor atom effects on copper(I)/O(2) chemistry with thioanisole containing tetradentate N(3)S ligand leading to μ-1,2-peroxo-dicopper(II) species.

2. Dioxygen activation at a single copper site: structure, bonding, and mechanism of formation of 1:1 Cu-O2 adducts.

3. Hydroxylation of phenolic compounds by a peroxodicopper(II) complex: further insight into the mechanism of tyrosinase.

4. Facile O-atom insertion into C-C and C-H bonds by a trinuclear copper complex designed to harness a singlet oxene.

5. Enzymatic C-H activation by metal-superoxo intermediates.

6. Investigation of the hydroxylation mechanism of noncoupled copper oxygenases by ab initio molecular dynamics simulations.

7. Evidence for Cu-O2 intermediates in superoxide oxidations by biomimetic copper(II) complexes.

8. Heterobimetallic dioxygen activation: synthesis and reactivity of mixed Cu-Pd and Cu-Pt bis(mu-oxo) complexes.

9. Effects of thioether substituents on the O2 reactivity of beta-diketiminate-Cu(I) complexes: probing the role of the methionine ligand in copper monooxygenases.

10. Geometric and electronic structure of [{Cu(MeAN)}2(μ-η2:η2(O2(2-)))]2+ with an unusually long O-O bond: O-O bond weakening vs activation for reductive cleavage.

1. Mechanisms for Hydrogen-Atom Abstraction by Mononuclear Copper(III) Cores: Hydrogen-Atom Transfer or Concerted Proton-Coupled Electron Transfer?

2. Intramolecular Hydrogen Bonding Enhances Stability and Reactivity of Mononuclear Cupric Superoxide Complexes.

3. Exclusive imidazole ligation to Cu^III₂O₂ and Cu^IIICu^II₂O₂ cores.

Review 4. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.

5. Determination of the Cu(III)-OH Bond Distance by Resonance Raman Spectroscopy Using a Normalized Version of Badger's Rule.

6. Impact of Intramolecular Hydrogen Bonding on the Reactivity of Cupric Superoxide Complexes with O-H and C-H Substrates.

7. Formally Copper(III)-Alkylperoxo Complexes as Models of Possible Intermediates in Monooxygenase Enzymes.

8. Reactivity of a stable copper-dioxygen complex.

9. Copper-Catalyzed Vinylogous Aerobic Oxidation of Unsaturated Compounds with Air.

10. Hydrogen Bonds Dictate O₂ Capture and Release within a Zinc Tripod.

Review 4. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Review 4. Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations.