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Enzyme-Like Hydroxylation of Aliphatic C?H Bonds From an Isolable Co-Oxo Complex

Journal Article · · J. Am. Chem. Soc.
DOI:https://doi.org/10.1021/jacs.1c09280· OSTI ID:1855480

Research Organization:
Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Sponsoring Organization:
DOE - Office Of Science; National Science Foundation (NSF)
OSTI ID:
1855480
Journal Information:
J. Am. Chem. Soc., Vol. 143, Issue (49)
Country of Publication:
United States
Language:
ENGLISH

References (88)

Aliphatic C–H Oxidations for Late-Stage Functionalization journal September 2018
The Quest for Selectivity in Hydrogen Atom Transfer Based Aliphatic C–H Bond Oxygenation journal August 2018
Hydrocarbon Hydroxylation by Cytochrome P450 Enzymes journal February 2010
Fe(II)/α-Ketoglutarate-Dependent Hydroxylases and Related Enzymes journal January 2004
Cytochrome P450 Compound I: Capture, Characterization, and C-H Bond Activation Kinetics journal November 2010
Iron(IV)hydroxide pKa and the Role of Thiolate Ligation in C-H Bond Activation by Cytochrome P450 journal November 2013
Reduction Potentials of P450 Compounds I and II: Insight into the Thermodynamics of C–H Bond Activation journal March 2019
Timing of the radical recombination step in cytochrome P-450 catalysis with ring-strained probes journal May 1987
Do spin state and spin density affect hydrogen atom transfer reactivity? journal January 2014
P450 Enzymes: Their Structure, Reactivity, and Selectivity—Modeled by QM/MM Calculations journal February 2010
Theoretical Perspective on the Structure and Mechanism of Cytochrome P450 Enzymes journal June 2005
Hydroxylation and epoxidation catalyzed by iron-porphine complexes. Oxygen transfer from iodosylbenzene journal February 1979
Aliphatic hydroxylation catalyzed by iron porphyrin complexes journal September 1983
Hydrocarbon oxidations with oxometalloporphinates. Isolation and reactions of a (porphinato)manganese(V) complex journal September 1980
Chemoselective Aliphatic C–H Bond Oxidation Enabled by Polarity Reversal journal December 2017
A Predictably Selective Aliphatic C H Oxidation Reaction for Complex Molecule Synthesis journal November 2007
Alkane functionalization by nonporphyrin iron complexes: mechanistic insights journal July 1990
High-valent iron-porphyrin complexes related to peroxidase and cytochrome P-450 journal May 1981
Synthesis, characterization, and reactivity of oxomanganese(IV) porphyrin complexes journal December 1988
Intramolecular kinetic isotope effects in alkane hydroxylations catalyzed by manganese and iron porphyrin complexes journal August 1993
Evidence for the participation of a high-valent iron–oxo species in stereospecific alkane hydroxylation by a non-heme iron catalyst journal January 1999
Molecular Designs for Controlling the Local Environments around Metal Ions journal July 2015
Semiempirical method for examining asynchronicity in metal–oxido-mediated C–H bond activation journal August 2021
Mn(V)(O) versus Cr(V)(O) Porphyrinoid Complexes: Structural Characterization and Implications for Basicity Controlling H-Atom Abstraction journal August 2015
Monomeric Mn III/II and Fe III/II Complexes with Terminal Hydroxo and Oxo Ligands:  Probing Reactivity via O−H Bond Dissociation Energies journal October 2003
Understanding the Selectivity of a Moderate Oxidation Catalyst:  Hydrogen Abstraction by a Fully Characterized, Activated Catalyst, the Robust Dihydroxo Manganese(IV) Complex of a Bridged Cyclam journal February 2007
Inertia and driving force of chemical reactions journal January 1938
Hydrocarbon Oxidation by an Exposed, Multiply Bonded Iron(III) Oxo Complex journal September 2021
Hydrogen tunneling in the activation of dioxygen by a tris(pyrazolyl)borate cobalt complex journal July 1994
M−O Bonding Beyond the Oxo Wall: Spectroscopy and Reactivity of Cobalt(III)-Oxyl and Cobalt(III)-Oxo Complexes journal June 2019
Aliphatic C−H Bond Oxygenation by the Co II OOX Species with the Hindered Hydrotris(pyrazolyl)borate Ligand (X = Co(II), Alkyl, H) journal May 1998
Structural Characterization and Intramolecular Aliphatic C−H Oxidation Ability of MIII(μ-O)2MIII Complexes of Ni and Co with the Hydrotris(3,5-dialkyl-4-X-pyrazolyl)borate Ligands TpMe2,X (X=Me, H, Br) and TpiPr2 journal December 2001
Oxidation of C−H Bonds by [(bpy) 2 (py)Ru IV O] 2+ Occurs by Hydrogen Atom Abstraction journal August 2003
C-H Bond Activation by Metal Oxo Species: Oxidation of Cyclohexane by Chromyl Chloride journal March 1994
Hydrogen Atom Abstraction by Permanganate:  Oxidations of Arylalkanes in Organic Solvents journal May 1997
Nonheme Fe IV O Complexes That Can Oxidize the C−H Bonds of Cyclohexane at Room Temperature journal January 2004
Spectroscopic Capture and Reactivity of a Low-Spin Cobalt(IV)-Oxo Complex Stabilized by Binding Redox-Inactive Metal Ions journal July 2014
Synthesis and reactivity of a mononuclear non-haem cobalt(IV)-oxo complex journal March 2017
Experimental Evidence for p K a -Driven Asynchronicity in C–H Activation by a Terminal Co(III)–Oxo Complex journal February 2019
The Oxo-Wall Remains Intact: A Tetrahedrally Distorted Co(IV)–Oxo Complex journal October 2021
Nickel( ii )-methyl complexes adopting unusual seesaw geometries journal January 2020
Isolation of a Terminal Co(III)-Oxo Complex journal August 2018
Removing the Sting from the Tail:  Reversible Protonation of Scorpionate Ligands in Cobalt(II) Tris(carbene)borate Complexes journal November 2006
Stereochemistry and Spin State in Four-Coordinate Transition Metal Compounds journal April 2008
Two, Three, or Not to Be? Elucidating Multiple Bonding in d 6 Pseudotetrahedral Oxo and Imide Complexes journal July 2021
An Acidity Scale for Phosphorus-Containing Compounds Including Metal Hydrides and Dihydrogen Complexes in THF:  Toward the Unification of Acidity Scales journal September 2000
Guanidinophosphazenes:  Design, Synthesis, and Basicity in THF and in the Gas Phase journal November 2005
Determination of the Cu(III)–OH Bond Distance by Resonance Raman Spectroscopy Using a Normalized Version of Badger’s Rule journal March 2017
Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications journal December 2010
Hydrogen Atom Abstraction from Hydrocarbons by a Copper(III)-Hydroxide Complex journal January 2015
Three-Coordinate Cobalt(IV) and Cobalt(V) Imido Complexes with N-Heterocyclic Carbene Ligation: Synthesis, Structure, and Their Distinct Reactivity in C–H Bond Amination journal October 2014
Crystal Structure and C–H Bond-Cleaving Reactivity of a Mononuclear Co IV –Dinitrate Complex journal July 2020
Rapid C–H Bond Activation by a Monocopper(III)–Hydroxide Complex journal November 2011
Mechanistic Study of the Oxidative N-Dealkylation Reactions of Bis(μ-oxo)dicopper Complexes journal January 1996
The Crystal Structure of a High-Spin Oxoiron(IV) Complex and Characterization of Its Self-Decay Pathway journal June 2010
Nuclear spin-spin coupling via nonbonded interactions. 2. .gamma.-Substituent effects for vicinal coupling constants involving carbon-13 journal January 1980
A critical evaluation of DFT, including time-dependent DFT, applied to bioinorganic chemistry journal July 2006
Elucidation of a Low Spin Cobalt(II) System in a Distorted Tetrahedral Geometry journal December 2002
Electronic Structure Description of a [Co(III) 3 Co(IV)O 4 ] Cluster: A Model for the Paramagnetic Intermediate in Cobalt-Catalyzed Water Oxidation journal October 2011
Electron Paramagnetic Resonance Characterization of Dioxygen-Bridged Cobalt Dimers with Relevance to Water Oxidation journal December 2016
Highly Reactive Co III,IV 2 (μ-O) 2 Diamond Core Complex That Cleaves C–H Bonds journal December 2019
An Intermediate Cobalt(IV) Nitrido Complex and its N-Migratory Insertion Product journal October 2014
Synthesis and characterization of stable cobalt(IV) coordination complexes: molecular structure of trans-[.eta.4-1,2-bis(3,5-dichloro-2-hydroxybenzamido)-4,5-dichlorobenzene]bis(4-tert-butylpyridine)cobalt(IV) journal August 1984
Organobis(dioximato)cobalt(IV) complexes: electron paramagnetic resonance spectra and electronic structures journal May 1979
Intrinsic Atomic Orbitals: An Unbiased Bridge between Quantum Theory and Chemical Concepts journal October 2013
cPCET versus HAT: A Direct Theoretical Method for Distinguishing X-H Bond-Activation Mechanisms journal August 2018
Solubility of hydrogen in 10 organic solvents at 298.15, 323.15, and 373.15 K journal July 1985
Reactivity of the copper( iii )-hydroxide unit with phenols journal January 2017
Generation and Reactivity of a Ni III 2 (μ-1,2-peroxo) Complex journal December 2020
Spin-State Tuning at Pseudotetrahedral d 7 Ions:  Examining the Structural and Magnetic Phenomena of Four-Coordinate [BP 3 ]Co II −X Systems journal May 2005
Quantitative analysis of dinuclear manganese(II) EPR spectra journal November 2003
The ORCA quantum chemistry program package journal June 2020
Left-right correlation energy journal March 2001
Dynamic correlation journal April 2001
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density journal January 1988
A Smooth Solvation Potential Based on the Conductor-Like Screening Model journal December 1999
Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy journal January 2005
Accurate Coulomb-fitting basis sets for H to Rn journal January 2006
Supramolecular Binding Thermodynamics by Dispersion-Corrected Density Functional Theory journal July 2012
The calculation of electron localization and delocalization indices at the Hartree-Fock, density functional and post-Hartree-Fock levels of theory journal June 2002
Comparison of the AIM Delocalization Index and the Mayer and Fuzzy Atom Bond Orders journal October 2005
Revitalizing the concept of bond order through delocalization measures in real space journal January 2018
A multicenter numerical integration scheme for polyatomic molecules journal February 1988
Multiwfn: A multifunctional wavefunction analyzer journal December 2011
Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination journal January 2015
SHELXT – Integrated space-group and crystal-structure determination journal January 2015
OLEX2 : a complete structure solution, refinement and analysis program journal January 2009
Crystal structure refinement with SHELXL journal January 2015