Beyond ferryl-mediated hydroxylation: 40 years of the rebound mechanism and C–H activation

Discovery of a Promiscuous Non-Heme Iron Halogenase in Ambiguine Alkaloid Biogenesis: Implication for an Evolvable Enzyme Family for Late-Stage Halogenation of Aliphatic Carbons in Small Molecules

(2016) Matthew L. Hillwig et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids

(2016) Jie Wang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Expanding the substrate scope and reactivity of cytochrome P450 OleT

(2016) Chun H. Hsieh et al.   BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS

Exploring substrate scope and stereoselectivity of P450 peroxygenase OleTJE in olefin-forming oxidative decarboxylation

(2016) Jian-bo Wang et al.   CHEMICAL COMMUNICATIONS

Transition-Metal Hydride Radical Cations

(2016) Yue Hu et al.   CHEMICAL REVIEWS

18F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography

(2016) Sean Preshlock et al.   CHEMICAL REVIEWS

To rebound or dissociate? This is the mechanistic question in C–H hydroxylation by heme and nonheme metal–oxo complexes

(2016) Kyung-Bin Cho et al.   CHEMICAL SOCIETY REVIEWS

The medicinal chemist's toolbox for late stage functionalization of drug-like molecules

(2016) Tim Cernak et al.   CHEMICAL SOCIETY REVIEWS

Origin of the Regioselective Fatty-Acid Hydroxylation versus Decarboxylation by a Cytochrome P450 Peroxygenase: What Drives the Reaction to Biofuel Production?

(2016) Abayomi S. Faponle et al.   CHEMISTRY-A EUROPEAN JOURNAL

Spectroscopic Evidence for the Two C–H-Cleaving Intermediates of Aspergillus nidulans Isopenicillin N Synthase

(2016) Esta Tamanaha et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Modeling Non-Heme Iron Halogenases: High-Spin Oxoiron(IV)–Halide Complexes That Halogenate C–H Bonds

(2016) Mayank Puri et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The Cytochrome P450-Catalyzed Oxidative Rearrangement in the Final Step of Pentalenolactone Biosynthesis: Substrate Structure Determines Mechanism

(2016) Lian Duan et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Radicals: Reactive Intermediates with Translational Potential

(2016) Ming Yan et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Structural basis for halogenation by iron- and 2-oxo-glutarate-dependent enzyme WelO5

(2016) Andrew J Mitchell et al.   Nature Chemical Biology

Catalytic strategy for carbon−carbon bond scission by the cytochrome P450 OleT

(2016) Job L. Grant et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Aryl amination using ligand-free Ni(II) salts and photoredox catalysis

(2016) Emily B. Corcoran et al.   SCIENCE

Asymmetric copper-catalyzed C-N cross-couplings induced by visible light

(2016) Q. M. Kainz et al.   SCIENCE

Undirected, Homogeneous C–H Bond Functionalization: Challenges and Opportunities

(2016) John F. Hartwig et al.   ACS Central Science

Late Stage Azidation of Complex Molecules

(2016) Rashad R. Karimov et al.   ACS Central Science

Photoredox Catalysis Unlocks Single-Electron Elementary Steps in Transition Metal Catalyzed Cross-Coupling

(2016) Mark D. Levin et al.   ACS Central Science

Manganese Catalyzed C–H Halogenation

(2015) Wei Liu et al.   ACCOUNTS OF CHEMICAL RESEARCH

Targeted Fluorination with the Fluoride Ion by Manganese-Catalyzed Decarboxylation

(2015) Xiongyi Huang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Catalysis of Radical Reactions: A Radical Chemistry Perspective

(2015) Armido Studer et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Evidence That Compound I Is the Active Species in Both the Hydroxylase and Lyase Steps by Which P450scc Converts Cholesterol to Pregnenolone: EPR/ENDOR/Cryoreduction/Annealing Studies

(2015) Roman Davydov et al.   BIOCHEMISTRY

Iron Catalysis in Organic Synthesis

(2015) Ingmar Bauer et al.   CHEMICAL REVIEWS

Ferryl Protonation in Oxoiron(IV) Porphyrins and Its Role in Oxygen Transfer

(2015) Nicholas C. Boaz et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A Common Late-Stage Intermediate in Catalysis by 2-Hydroxyethyl-phosphonate Dioxygenase and Methylphosphonate Synthase

(2015) Spencer C. Peck et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Mechanism of Oxygen Activation in a Flavin-Dependent Monooxygenase: A Nearly Barrierless Formation of C4a-Hydroperoxyflavin via Proton-Coupled Electron Transfer

(2015) Surawit Visitsatthawong et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Rapid Reduction of the Diferric-Peroxyhemiacetal Intermediate in Aldehyde-Deformylating Oxygenase by a Cyanobacterial Ferredoxin: Evidence for a Free-Radical Mechanism

(2015) Lauren J. Rajakovich et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Merging Photoredox and Nickel Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Vinyl Halides

(2015) Adam Noble et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Experimental Correlation of Substrate Position with Reaction Outcome in the Aliphatic Halogenase, SyrB2

(2015) Ryan J. Martinie et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Decarboxylation of Fatty Acids to Terminal Alkenes by Cytochrome P450 Compound I

(2015) Job L. Grant et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Manganese-Catalyzed Late-Stage Aliphatic C–H Azidation

(2015) Xiongyi Huang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Evolution of C–H Bond Functionalization from Methane to Methodology

(2015) John F. Hartwig   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Structure of the key species in the enzymatic oxidation of methane to methanol

(2015) Rahul Banerjee et al.   NATURE

Metal-catalysed azidation of tertiary C–H bonds suitable for late-stage functionalization

(2015) Ankit Sharma et al.   NATURE

Taming Azide Radicals for Catalytic C–H Azidation

(2015) Xiongyi Huang et al.   ACS Catalysis

Iron(II) Catalysis in Oxidation of Hydrocarbons with Ozone in Acetonitrile

(2015) Hajem Bataineh et al.   ACS Catalysis

Structural modeling of iron halogenases: synthesis and reactivity of halide-iron(iv)-oxo compounds

(2014) Oriol Planas et al.   CHEMICAL COMMUNICATIONS

Mechanistic Consequences of Chiral Radical Clock Probes: Analysis of the Mononuclear Non-Heme Iron Enzyme HppE with 2-Hydroxy-3-methylenecyclopropyl Radical Clock Substrates

(2014) Hui Huang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Direct, Catalytic Monofluorination of sp3 C–H Bonds: A Radical-Based Mechanism with Ionic Selectivity

(2014) Cody Ross Pitts et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Mechanism of the Third Oxidative Step in the Conversion of Androgens to Estrogens by Cytochrome P450 19A1 Steroid Aromatase

(2014) Francis K. Yoshimoto et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Selective Monooxidation of Light Alkanes Using Chloride and Iodate

(2014) George C. Fortman et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Late Stage Benzylic C–H Fluorination with [18F]Fluoride for PET Imaging

(2014) Xiongyi Huang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A new family of iron-dependent halogenases acts on freestanding substrates

(2014) Matthew L Hillwig et al.   Nature Chemical Biology

Direct nitration and azidation of aliphatic carbons by an iron-dependent halogenase

(2014) Megan L Matthews et al.   Nature Chemical Biology

Using push to get pull

(2014) John T. Groves   Nature Chemistry

Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis

(2014) J. C. Tellis et al.   SCIENCE

Merging photoredox with nickel catalysis: Coupling of  -carboxyl sp3-carbons with aryl halides

(2014) Z. Zuo et al.   SCIENCE

Late-stage [18F]fluorination: new solutions to old problems

(2014) Allen F. Brooks et al.   Chemical Science

Driving Force for Oxygen-Atom Transfer by Heme-Thiolate Enzymes

(2013) Xiaoshi Wang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Click Chemistry for Drug Development and Diverse Chemical–Biology Applications

(2013) Prakasam Thirumurugan et al.   CHEMICAL REVIEWS

Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis

(2013) Christopher K. Prier et al.   CHEMICAL REVIEWS

Does the Oxidation of Nitric Oxide by oxyMyoglobin Share an Intermediate with the metMyoglobin-Catalyzed Isomerization of Peroxynitrite?

(2013) Karl J. Koebke et al.   INORGANIC CHEMISTRY

Substrate Placement Influences Reactivity in Non-heme Fe(II) Halogenases and Hydroxylases

(2013) Heather J. Kulik et al.   JOURNAL OF BIOLOGICAL CHEMISTRY

Reaction of HppE with Substrate Analogues: Evidence for Carbon–Phosphorus Bond Cleavage by a Carbocation Rearrangement

(2013) Wei-chen Chang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Visible Light-Promoted Metal-Free C–H Activation: Diarylketone-Catalyzed Selective Benzylic Mono- and Difluorination

(2013) Ji-Bao Xia et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Elucidation of the Fe(iv)=O intermediate in the catalytic cycle of the halogenase SyrB2

(2013) Shaun D. Wong et al.   NATURE

Metal-Free Fluorination of C(sp3)–H Bonds Using a Catalytic N-Oxyl Radical

(2013) Yuuki Amaoka et al.   ORGANIC LETTERS

Evidence that the Fosfomycin-Producing Epoxidase, HppE, Is a Non-Heme-Iron Peroxidase

(2013) C. Wang et al.   SCIENCE

Iron(IV)hydroxide pKa and the Role of Thiolate Ligation in C-H Bond Activation by Cytochrome P450

(2013) T. H. Yosca et al.   SCIENCE

When C–H bond functionalization meets visible-light photoredox catalysis

(2013) Jin Xie et al.   TETRAHEDRON LETTERS

Correlating DFT-Calculated Energy Barriers to Experiments in Nonheme Octahedral FeIVO Species

(2012) Kyung-Bin Cho et al.   CHEMISTRY-A EUROPEAN JOURNAL

First Crystal Structure of a Fungal High-redox Potential Dye-decolorizing Peroxidase

(2012) Eric Strittmatter et al.   JOURNAL OF BIOLOGICAL CHEMISTRY

Theoretical Investigations into C–H Bond Activation Reaction by Nonheme MnIVO Complexes: Multistate Reactivity with No Oxygen Rebound

(2012) Kyung-Bin Cho et al.   Journal of Physical Chemistry Letters

Fluorine Transfer to Alkyl Radicals

(2012) Montserrat Rueda-Becerril et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Mechanistic Investigation of Methylphosphonate Synthase, a Non-Heme Iron-Dependent Oxygenase

(2012) Heather A. Cooke et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Detection and Kinetic Characterization of a Highly Reactive Heme–Thiolate Peroxygenase Compound I

(2012) Xiaoshi Wang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Parallel and Competitive Pathways for Substrate Desaturation, Hydroxylation, and Radical Rearrangement by the Non-heme Diiron Hydroxylase AlkB

(2012) Harriet L. R. Cooper et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Evidence for an Alternative to the Oxygen Rebound Mechanism in C–H Bond Activation by Non-Heme FeIVO Complexes

(2012) Kyung-Bin Cho et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in the Copper-Catalyzed Trifluoromethylation of Boronic Acids with CF3I

(2012) Yingda Ye et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin

(2012) W. Liu et al.   SCIENCE

Synthesis of Methylphosphonic Acid by Marine Microbes: A Source for Methane in the Aerobic Ocean

(2012) W. W. Metcalf et al.   SCIENCE

The enigmatic reaction of flavins with oxygen

(2012) Pimchai Chaiyen et al.   TRENDS IN BIOCHEMICAL SCIENCES

pH-induced mechanistic changeover from hydroxyl radicals to iron(iv) in the Fenton reaction

(2012) Hajem Bataineh et al.   Chemical Science

The biology and chemistry of high-valent iron–oxo and iron–nitrido complexes

(2012) Johannes Hohenberger et al.   Nature Communications

Terminal Olefin (1-Alkene) Biosynthesis by a Novel P450 Fatty Acid Decarboxylase fromJeotgalicoccusSpecies

(2011) Mathew A. Rude et al.   APPLIED AND ENVIRONMENTAL MICROBIOLOGY

Transition metal catalysis and nucleophilic fluorination

(2011) Charlotte Hollingworth et al.   CHEMICAL COMMUNICATIONS

Selective functionalisation of saturated C–H bonds with metalloporphyrin catalysts

(2011) Chi-Ming Che et al.   CHEMICAL SOCIETY REVIEWS

Structural Basis of Regiospecificity of a Mononuclear Iron Enzyme in Antibiotic Fosfomycin Biosynthesis

(2011) Danny Yun et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Oxygen Reactivity in Flavoenzymes: Context Matters

(2011) Claudia A. McDonald et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Catalysis for fluorination and trifluoromethylation

(2011) Takeru Furuya et al.   NATURE

Understanding Hydrogen Atom Transfer: From Bond Strengths to Marcus Theory

(2010) James M. Mayer   ACCOUNTS OF CHEMICAL RESEARCH

Analysis of Reaction Channels for Alkane Hydroxylation by Nonheme Iron(IV)-Oxo Complexes

(2010) Caiyun Geng et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Molecular probes of the mechanism of cytochrome P450. Oxygen traps a substrate radical intermediate

(2010) Harriet L.R. Cooper et al.   ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS

Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions

(2010) Thomas W. Lyons et al.   CHEMICAL REVIEWS

Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications

(2010) Jeffrey J. Warren et al.   CHEMICAL REVIEWS

Enzymatic functionalization of carbon–hydrogen bonds

(2010) Jared C. Lewis et al.   CHEMICAL SOCIETY REVIEWS

Iron-Catalyzed Halogenation of Alkanes: Modeling of Nonheme Halogenases by Experiment and DFT Calculations

(2010) Peter Comba et al.   CHEMISTRY-A EUROPEAN JOURNAL

Mechanisms of Peroxynitrite Interactions with Heme Proteins

(2010) Jia Su et al.   INORGANIC CHEMISTRY

Protein Free Energy Corrections in ONIOM QM:MM Modeling: A Case Study for Isopenicillin N Synthase (IPNS)

(2010) Tsutomu Kawatsu et al.   Journal of Chemical Theory and Computation

Manganese Catalysts for C−H Activation: An Experimental/Theoretical Study Identifies the Stereoelectronic Factor That Controls the Switch between Hydroxylation and Desaturation Pathways

(2010) Jonathan F. Hull et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Manganese Porphyrins Catalyze Selective C−H Bond Halogenations

(2010) Wei Liu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Cytochrome P450 Compound I: Capture, Characterization, and C-H Bond Activation Kinetics

(2010) J. Rittle et al.   SCIENCE

Substrate-Triggered Formation and Remarkable Stability of the C−H Bond-Cleaving Chloroferryl Intermediate in the Aliphatic Halogenase, SyrB2

(2009) Megan L. Matthews et al.   BIOCHEMISTRY

Hydrocarbon Hydroxylation by Cytochrome P450 Enzymes

(2009) Paul R. Ortiz de Montellano   CHEMICAL REVIEWS

Rhodium-Catalyzed C−C Bond Formation via Heteroatom-Directed C−H Bond Activation

(2009) Denise A. Colby et al.   CHEMICAL REVIEWS

CH bond activation in heme proteins: the role of thiolate ligation in cytochrome P450

(2009) Michael T Green   CURRENT OPINION IN CHEMICAL BIOLOGY

Solvent-Dependent Cage Dynamics of Small Nonpolar Radicals: Lessons from the Photodissociation and Geminate Recombination of Alkylcobalamins

(2009) Andrew B. Stickrath et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Direct Detection of the Oxygen Rebound Intermediates, Ferryl Mb and NO2, in the Reaction of metMyoglobin with Peroxynitrite

(2009) Jia Su et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Quantitative Production of Compound I from a Cytochrome P450 Enzyme at Low Temperatures. Kinetics, Activation Parameters, and Kinetic Isotope Effects for Oxidation of Benzyl Alcohol

(2009) Qin Wang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A Highly Reactive P450 Model Compound I

(2009) Seth R. Bell et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Structural Analysis of an Open Active Site Conformation of Nonheme Iron Halogenase CytC3

(2009) Cintyu Wong et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

First-Principles Study of Non-heme Fe(II) Halogenase SyrB2 Reactivity

(2009) Heather J. Kulik et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Substrate positioning controls the partition between halogenation and hydroxylation in the aliphatic halogenase, SyrB2

(2009) M. L. Matthews et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Cage Escape Competes with Geminate Recombination during Alkane Hydroxylation by the Diiron Oxygenase AlkB

(2008) Rachel N. Austin et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Synthesis of11C,18F,15O, and13N Radiolabels for Positron Emission Tomography

(2008) Philip W. Miller et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Mononuclear non-heme iron enzymes with the 2-His-1-carboxylate facial triad: recent developments in enzymology and modeling studies

(2008) Pieter C. A. Bruijnincx et al.   CHEMICAL SOCIETY REVIEWS

Transition States in a Protein Environment − ONIOM QM:MM Modeling of Isopenicillin N Synthesis

(2008) Marcus Lundberg et al.   Journal of Chemical Theory and Computation

Biologically inspired oxidation catalysis

(2008) Lawrence Que et al.   NATURE

Versatility of biological non-heme Fe(II) centers in oxygen activation reactions

(2008) Elena G Kovaleva et al.   Nature Chemical Biology

The Mechanism for Isopenicillin N Synthase from Density-Functional Modeling Highlights the Similarities with Other Enzymes in the 2-His-1-carboxylate Family†

(2007) Marcus Lundberg et al.   BIOCHEMISTRY

The rebound mechanism in catalytic C–H oxidation by MnO(tpp)Cl from DFT studies: electronic nature of the active species

(2007) David Balcells et al.   CHEMICAL COMMUNICATIONS

Understanding organofluorine chemistry. An introduction to the C–F bond

(2007) David O'Hagan   CHEMICAL SOCIETY REVIEWS