Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities

Tuning Reactivity and Selectivity in Hydrogen Atom Transfer from Aliphatic C–H Bonds to Alkoxyl Radicals: Role of Structural and Medium Effects

(2015) Michela Salamone et al.   ACCOUNTS OF CHEMICAL RESEARCH

Photoredox-Catalyzed Reductive Coupling of Aldehydes, Ketones, and Imines with Visible Light

(2015) Masaki Nakajima et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Moving Protons and Electrons in Biomimetic Systems

(2015) Jeffrey J. Warren et al.   BIOCHEMISTRY

Proton-coupled electron transfer with photoexcited ruthenium(II), rhenium(I), and iridium(III) complexes

(2015) Oliver S. Wenger   COORDINATION CHEMISTRY REVIEWS

Concerted Electron–Proton Transfer (EPT) in the Oxidation of Cysteine

(2015) Christopher J. Gagliardi et al.   Journal of Physical Chemistry C

Light-Driven, Proton-Controlled, Catalytic Aerobic C–H Oxidation Mediated by a Mn(III) Porphyrinoid Complex

(2015) Heather M. Neu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Mn(V)(O) versus Cr(V)(O) Porphyrinoid Complexes: Structural Characterization and Implications for Basicity Controlling H-Atom Abstraction

(2015) Regina A. Baglia et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

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

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

Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron Transfer

(2015) David C. Miller et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Bond-Weakening Catalysis: Conjugate Aminations Enabled by the Soft Homolysis of Strong N–H Bonds

(2015) Kyle T. Tarantino et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Catalytic Alkene Carboaminations Enabled by Oxidative Proton-Coupled Electron Transfer

(2015) Gilbert J. Choi 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

High-spin Mn–oxo complexes and their relevance to the oxygen-evolving complex within photosystem II

(2015) Rupal Gupta et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Late-Stage Functionalization of Biologically Active Heterocycles Through Photoredox Catalysis

(2014) Daniel A. DiRocco et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Concerted Proton-Electron Transfers: Fundamentals and Recent Developments

(2014) Jean-Michel Savéant   Annual Review of Analytical Chemistry

Biochemistry and Theory of Proton-Coupled Electron Transfer

(2014) Agostino Migliore et al.   CHEMICAL REVIEWS

Thiyl Radicals in Organic Synthesis

(2014) Fabrice Dénès et al.   CHEMICAL REVIEWS

Mechanistic Study of the Titanocene(III)-Catalyzed Radical Arylation of Epoxides

(2014) Andreas Gansäuer et al.   CHEMISTRY-A EUROPEAN JOURNAL

Distance Dependence of Bidirectional Concerted Proton-Electron Transfer in Phenol-Ru(2,2′-bipyridine)32+Dyads

(2014) Jing Chen et al.   CHEMISTRY-A EUROPEAN JOURNAL

Redox Mediators in Visible Light Photocatalysis: Photocatalytic Radical Thiol–Ene Additions

(2014) Elizabeth L. Tyson et al.   JOURNAL OF ORGANIC CHEMISTRY

N–N Bond Cleavage of 1,2-Diarylhydrazines and N–H Bond Formation via H-Atom Transfer in Vanadium Complexes Supported by a Redox-Active Ligand

(2014) Carsten Milsmann et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Photochemical Tyrosine Oxidation in the Structurally Well-Defined α3Y Protein: Proton-Coupled Electron Transfer and a Long-Lived Tyrosine Radical

(2014) Starla D. Glover et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A Practical and Catalytic Reductive Olefin Coupling

(2014) Julian C. Lo et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Water Promoting Electron Hole Transport between Tyrosine and Cysteine in Proteins via a Special Mechanism: Double Proton Coupled Electron Transfer

(2014) Xiaohua Chen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The Reaction of Cobaloximes with Hydrogen: Products and Thermodynamics

(2014) Deven P. Estes et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Four-Coordinate Cobalt Pincer Complexes: Electronic Structure Studies and Ligand Modification by Homolytic and Heterolytic Pathways

(2014) Scott P. Semproni et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Setting an Upper Limit on the Myoglobin Iron(IV)Hydroxide pKa: Insight into Axial Ligand Tuning in Heme Protein Catalysis

(2014) Timothy H. Yosca et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Simple, Chemoselective Hydrogenation with Thermodynamic Stereocontrol

(2014) Kotaro Iwasaki et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A Method for the Selective Hydrogenation of Alkenyl Halides to Alkyl Halides

(2014) Sandra M. King et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Activation of C–H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases

(2014) Dominik Hager et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A bioinspired redox relay that mimics radical interactions of the Tyr–His pairs of photosystem II

(2014) Jackson D. Megiatto Jr et al.   Nature Chemistry

Preparation and properties of an MnIV–hydroxide complex: proton and electron transfer at a mononuclear manganese site and its relationship to the oxygen evolving complex within photosystem II

(2014) Taketo Taguchi et al.   Chemical Science

Proton-Coupled Electron Transfer with Photoexcited Metal Complexes

(2013) Oliver S. Wenger   ACCOUNTS OF CHEMICAL RESEARCH

Reversible, Long-Range Radical Transfer in E. coli Class Ia Ribonucleotide Reductase

(2013) Ellen C. Minnihan et al.   ACCOUNTS OF CHEMICAL RESEARCH

Oxidation of water by a nonhaem diiron(iv) complex via proton-coupled electron transfer

(2013) Dong Wang et al.   CHEMICAL COMMUNICATIONS

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

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

Electrostatic Effects on Proton Coupled Electron Transfer in Oxomanganese Complexes Inspired by the Oxygen-Evolving Complex of Photosystem II

(2013) Muhamed Amin et al.   JOURNAL OF PHYSICAL CHEMISTRY B

Long-Range Proton-Coupled Electron-Transfer Reactions of Bis(imidazole) Iron Tetraphenylporphyrins Linked to Benzoates

(2013) Jeffrey J. Warren et al.   Journal of Physical Chemistry Letters

Mechanistic Diversity in Proton-Coupled Electron Transfer between Thiophenols and Photoexcited [Ru(2,2′-Bipyrazine)3]2+

(2013) Martin Kuss-Petermann et al.   Journal of Physical Chemistry Letters

Electrochemical Evidence for Intermolecular Proton-Coupled Electron Transfer through a Hydrogen Bond Complex in a p-Phenylenediamine-Based Urea. Introduction of the “Wedge Scheme” as a Useful Means To Describe Reactions of This Type

(2013) Laurie A. Clare et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Brønsted Acid-Promoted C–H Bond Cleavage via Electron Transfer from Toluene Derivatives to a Protonated Nonheme Iron(IV)-Oxo Complex with No Kinetic Isotope Effect

(2013) Jiyun Park et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Silver-Catalyzed Radical Aminofluorination of Unactivated Alkenes in Aqueous Media

(2013) Zhaodong Li et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A General Strategy for Organocatalytic Activation of C–H Bonds via Photoredox Catalysis: Direct Arylation of Benzylic Ethers

(2013) Katrine Qvortrup et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective Photoredox Catalysis Enabled by Proton-Coupled Electron Transfer: Development of an Asymmetric Aza-Pinacol Cyclization

(2013) Lydia J. Rono et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Catalytic Ketyl-Olefin Cyclizations Enabled by Proton-Coupled Electron Transfer

(2013) Kyle T. Tarantino et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Germanium(iii) corrole complex: reactivity and mechanistic studies of visible-light promoted N–H bond activations

(2013) Huayi Fang et al.   Chemical Science

Proton-Coupled Electron Transfer

(2012) David R. Weinberg et al.   CHEMICAL REVIEWS

Using combinations of oxidants and bases as PCET reactants: thermochemical and practical considerations

(2012) Christopher R. Waidmann et al.   Energy & Environmental Science

Bimolecular proton-coupled electron transfer from tryptophan with water as the proton acceptor

(2012) Ming-Tian Zhang et al.   Energy & Environmental Science

Proton-coupled electron transfer: classification scheme and guide to theoretical methods

(2012) Sharon Hammes-Schiffer   Energy & Environmental Science

Pourbaix (E–pH-M) Diagrams in Three Dimensions

(2012) Lester L. Pesterfield et al.   JOURNAL OF CHEMICAL EDUCATION

Effect of Basic Site Substituents on Concerted Proton–Electron Transfer in Hydrogen-Bonded Pyridyl–Phenols

(2012) Todd F. Markle et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Buffer Effects in the Kinetics of Concerted Proton-Coupled Electron Transfer: The Electrochemical Oxidation of Glutathione Mediated by [IrCl6]2–at Variable Buffer pKa and Concentration

(2012) Jonnathan Medina-Ramos et al.   Journal of Physical Chemistry C

Proton-Promoted Oxygen Atom Transfer vs Proton-Coupled Electron Transfer of a Non-Heme Iron(IV)-Oxo Complex

(2012) Jiyun Park et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Multiple-Site Concerted Proton–Electron Transfer Reactions of Hydrogen-Bonded Phenols Are Nonadiabatic and Well Described by Semiclassical Marcus Theory

(2012) Joel N. Schrauben et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Reversible voltammograms and a Pourbaix diagram for a protein tyrosine radical

(2012) B. W. Berry et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

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

(2012) W. Liu et al.   SCIENCE

A Local Proton Source Enhances CO2 Electroreduction to CO by a Molecular Fe Catalyst

(2012) C. Costentin et al.   SCIENCE

Photochemical tyrosine oxidation with a hydrogen-bonded proton acceptor by bidirectional proton-coupled electron transfer

(2012) Arturo A. Pizano et al.   Chemical Science

Blended hydrogen atom abstraction and proton-coupled electron transfer mechanisms of closed-shell molecules

(2012) Chunsen Li et al.   Chemical Science

Role of metal–oxo complexes in the cleavage of C–H bonds

(2011) A. S. Borovik   CHEMICAL SOCIETY REVIEWS

Radical-Transfer Hydroamination of Olefins with N-Aminated Dihydropyridines

(2011) Chih-Ming Chou et al.   Chemistry-An Asian Journal

Dissection of the Mechanism of Manganese Porphyrin-Catalyzed Chlorine Dioxide Generation

(2011) Thomas P. Umile et al.   INORGANIC CHEMISTRY

The Role of Intermolecular Hydrogen Bonding and Proton Transfer in Proton-Coupled Electron Transfer

(2011) Timothy M. Alligrant et al.   Journal of Physical Chemistry C

Kinetic Isotope Effects in Reductive Excited-State Quenching of Ru(2,2′-bipyrazine)32+ by Phenols

(2011) Catherine Bronner et al.   Journal of Physical Chemistry Letters

Simple Marcus-Theory-Type Model for Hydrogen-Atom Transfer/Proton-Coupled Electron Transfer

(2011) James M. Mayer   Journal of Physical Chemistry Letters

Proton-Coupled Electron Transfer from Tryptophan: A Concerted Mechanism with Water as Proton Acceptor

(2011) Ming-Tian Zhang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Concerted Electron–Proton Transfer (EPT) in the Oxidation of Tryptophan with Hydroxide as a Base

(2011) Christopher J. Gagliardi et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Evidence for Concerted Electron Proton Transfer in Charge Recombination between FADH–and306Trp•inEscherichia coliPhotolyase

(2011) Agnieszka A. Zieba et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Electron- and Hydride-Transfer Reactivity of an Isolable Manganese(V)−Oxo Complex

(2011) Shunichi Fukuzumi et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Proton-Coupled Electron Transfer Reactions at a Heme-Propionate in an Iron-Protoporphyrin-IX Model Compound

(2011) Jeffrey J. Warren et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Electrochemical and Structural Properties of a Protein System Designed To Generate Tyrosine Pourbaix Diagrams

(2011) Melissa C. Martínez-Rivera et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Catalytic Reduction of Dioxygen to Water with a Monomeric Manganese Complex at Room Temperature

(2011) Ryan L. Shook et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Bidirectional and Unidirectional PCET in a Molecular Model of a Cobalt-Based Oxygen-Evolving Catalyst

(2011) Mark D. Symes et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Hydrogen Bonding of Tryptophan Radicals Revealed by EPR at 700 GHz

(2011) Stefan Stoll et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Concerted electron-proton transfer in the optical excitation of hydrogen-bonded dyes

(2011) B. C. Westlake et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Photocatalytic reductive cyclizations of enones: Divergent reactivity of photogenerated radical and radical anion intermediates

(2011) Juana Du et al.   Chemical Science

Understanding Hydrogen Atom Transfer: From Bond Strengths to Marcus Theory

(2010) James M. Mayer   ACCOUNTS OF CHEMICAL RESEARCH

Unprecedented Rate Enhancements of Hydrogen-Atom Transfer to a Manganese(V)-Oxo Corrolazine Complex

(2010) Katharine A. Prokop et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Inserting a Hydrogen-Bond Relay between Proton Exchanging Sites in Proton-Coupled Electron Transfers

(2010) Cyrille Costentin et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Catalytic Generation of Chlorine Dioxide from Chlorite Using a Water-Soluble Manganese Porphyrin

(2010) Thomas P. Umile et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Thiol-Ene Click Chemistry

(2010) Charles E. Hoyle et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Proton-Coupled Electron Transfer in Cytochrome Oxidase

(2010) Ville R. I. Kaila et al.   CHEMICAL REVIEWS

Proton-Coupled Electron Flow in Protein Redox Machines

(2010) Jillian L. Dempsey et al.   CHEMICAL REVIEWS

Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications

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

Integrating proton coupled electron transfer (PCET) and excited states

(2010) Christopher J. Gagliardi et al.   COORDINATION CHEMISTRY REVIEWS

Probing the Arenium-Ion (ProtonTransfer) versus the Cation-Radical (Electron Transfer) Mechanism of Scholl Reaction Using DDQ as Oxidant

(2010) Linyi Zhai et al.   JOURNAL OF ORGANIC CHEMISTRY

Manganese Porphyrins Catalyze Selective C−H Bond Halogenations

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

Proton-Coupled Electron Transfer in Biology: Results from Synergistic Studies in Natural and Model Systems

(2009) Steven Y. Reece et al.   Annual Review of Biochemistry

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

(2009) Michael T Green   CURRENT OPINION IN CHEMICAL BIOLOGY

Cyclometalated Iridium(III) Complexes as Photosensitizers for Long-Range Electron Transfer: Occurrence of a Coulomb Barrier

(2009) David Hanss et al.   EUROPEAN JOURNAL OF INORGANIC CHEMISTRY

Mapping Proton Wires in Proteins: Carbonic Anhydrase and GFP Chromophore Biosynthesis†

(2009) Ai Shinobu et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Analysis of Kinetic Isotope Effects for Proton-Coupled Electron Transfer Reactions†

(2009) Sarah J. Edwards et al.   JOURNAL OF PHYSICAL CHEMISTRY A

Comparative PCET Study of a Donor−Acceptor Pair Linked by Ionized and Nonionized Asymmetric Hydrogen-Bonded Interfaces

(2009) Elizabeth R. Young et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Theoretical and Experimental Studies of the Conversion of Chromopyrrolic Acid to an Antitumor Derivative by Cytochrome P450 StaP: The Catalytic Role of Water Molecules

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

Proton-Coupled Electron Transfer of Ruthenium(III)−Pterin Complexes: A Mechanistic Insight

(2009) Soushi Miyazaki et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Crossed Intermolecular [2+2] Cycloadditions of Acyclic Enones via Visible Light Photocatalysis

(2009) Juana Du et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

C−H Bond Cleavage with Reductants: Re-Investigating the Reactivity of Monomeric MnIII/IV−Oxo Complexes and the Role of Oxo Ligand Basicity

(2009) Trenton H. Parsell et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Concerted Proton−Electron Transfer in a Ruthenium Terpyridyl-Benzoate System with a Large Separation between the Redox and Basic Sites

(2009) Virginia W. Manner et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Influence of the Nitrogen Donors on Nonheme Iron Models of Superoxide Reductase: High-Spin FeIII−OOR Complexes

(2009) Frances Namuswe et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A diiron(iv) complex that cleaves strong C–H and O–H bonds

(2009) Dong Wang et al.   Nature Chemistry

The electrochemical approach to concerted proton--electron transfers in the oxidation of phenols in water

(2009) C. Costentin et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Proton-Coupled Electron Transfer in Solution, Proteins, and Electrochemistry†

(2008) Sharon Hammes-Schiffer et al.   JOURNAL OF PHYSICAL CHEMISTRY B

One-Step versus Stepwise Mechanism in Protonated Amino Acid-Promoted Electron-Transfer Reduction of a Quinone by Electron Donors and Two-Electron Reduction by a Dihydronicotinamide Adenine Dinucleotide Analogue. Interplay between Electron Transfer and Hydrogen Bonding

(2008) Junpei Yuasa et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Unusually Weak Metal−Hydrogen Bonds in HV(CO)4(P−P) and Their Effectiveness as H•Donors

(2008) Jongwook Choi et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Hydrogen Atom Transfer Reactions of a Ruthenium Imidazole Complex: Hydrogen Tunneling and the Applicability of the Marcus Cross Relation

(2008) Adam Wu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Electron Transfer Activation of Chromopyrrolic Acid by Cytochrome P450 En Route to the Formation of an Antitumor Indolocarbazole Derivative: Theory Supports Experiment

(2008) Yong Wang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Efficient Visible Light Photocatalysis of [2+2] Enone Cycloadditions

(2008) Michael A. Ischay et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Probing concerted proton-electron transfer in phenol-imidazoles

(2008) T. F. Markle et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Tryptophan-Accelerated Electron Flow Through Proteins

(2008) C. Shih et al.   SCIENCE

Concerted Proton–Electron Transfer in Pyridylphenols: The Importance of the Hydrogen Bond

(2007) Todd F. Markle et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Thiol-Catalyzed Stereoselective Transfer Hydroamination of Olefins with N-Aminated Dihydropyridines

(2007) Joyram Guin et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION