Studies of C–H Activation and Functionalization: Combined Computational and Experimental Efforts to Elucidate Mechanisms, Principles, and Catalysts

[1]  W. Goddard,et al.  DFT Mechanistic Study of Methane Mono-Esterification by Hypervalent Iodine Alkane Oxidation Process , 2019, The Journal of Physical Chemistry C.

[2]  W. Goddard,et al.  Mechanism of Hydrocarbon Functionalization by an Iodate/Chloride System: The Role of Ester Protection , 2018 .

[3]  W. Goddard,et al.  Probing the C–O Bond-Formation Step in Metalloporphyrin-Catalyzed C–H Oxygenation Reactions , 2017 .

[4]  Junqi Chen,et al.  Catalytic Synthesis of "Super" Linear Alkenyl Arenes Using an Easily Prepared Rh(I) Catalyst. , 2017, Journal of the American Chemical Society.

[5]  P. Schreiner,et al.  Mild Aliphatic and Benzylic Hydrocarbon C-H Bond Chlorination Using Trichloroisocyanuric Acid. , 2017, The Journal of organic chemistry.

[6]  Guido Zichittella,et al.  Catalytic Oxychlorination versus Oxybromination for Methane Functionalization , 2017 .

[7]  T. Cundari,et al.  Mechanistic Studies of Single-Step Styrene Production Using a Rhodium(I) Catalyst. , 2017, Journal of the American Chemical Society.

[8]  J. Groves,et al.  Beyond ferryl-mediated hydroxylation: 40 years of the rebound mechanism and C–H activation , 2016, JBIC Journal of Biological Inorganic Chemistry.

[9]  Thomas Kohl,et al.  The BioSCWG Project: Understanding the Trade-Offs in the Process and Thermal Design of Hydrogen and Synthetic Natural Gas Production , 2016 .

[10]  P. Baran,et al.  Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids. , 2016, Angewandte Chemie.

[11]  Ian W. Davies,et al.  Aryl amination using ligand-free Ni(II) salts and photoredox catalysis , 2016, Science.

[12]  W. Goddard,et al.  Transition-Metal-Mediated Nucleophilic Aromatic Substitution with Acids , 2016 .

[13]  F. Toste,et al.  Photoredox Catalysis Unlocks Single-Electron Elementary Steps in Transition Metal Catalyzed Cross-Coupling , 2016, ACS central science.

[14]  L. Que,et al.  Modeling Non-Heme Iron Halogenases: High-Spin Oxoiron(IV)-Halide Complexes That Halogenate C-H Bonds. , 2016, Journal of the American Chemical Society.

[15]  G. C. Fu,et al.  Asymmetric copper-catalyzed C-N cross-couplings induced by visible light , 2016, Science.

[16]  J. Groves,et al.  Taming Azide Radicals for Catalytic C–H Azidation , 2016 .

[17]  J. Hartwig Evolution of C-H Bond Functionalization from Methane to Methodology. , 2016, Journal of the American Chemical Society.

[18]  A. Studer,et al.  Catalysis of Radical Reactions: A Radical Chemistry Perspective. , 2016, Angewandte Chemie.

[19]  Mikhail Zhizhin,et al.  Methods for Global Survey of Natural Gas Flaring from Visible Infrared Imaging Radiometer Suite Data , 2015 .

[20]  W. Brennessel,et al.  Electrophilic C–H activation of benzene with a Shilov-inspired rhodium(III) diimine complex , 2015 .

[21]  F. Gallou,et al.  Nucleophilic Aromatic Substitution Reactions in Water Enabled by Micellar Catalysis. , 2015, Organic letters.

[22]  J. Groves,et al.  Manganese Catalyzed C-H Halogenation. , 2015, Accounts of chemical research.

[23]  C. Krebs,et al.  Experimental Correlation of Substrate Position with Reaction Outcome in the Aliphatic Halogenase, SyrB2. , 2015, Journal of the American Chemical Society.

[24]  J. Groves,et al.  Manganese-catalyzed late-stage aliphatic C-H azidation. , 2015, Journal of the American Chemical Society.

[25]  J. Groves,et al.  Heme-thiolate ferryl of aromatic peroxygenase is basic and reactive , 2015, Proceedings of the National Academy of Sciences.

[26]  J. Groves,et al.  Partial oxidation of light alkanes by periodate and chloride salts. , 2015, Dalton transactions.

[27]  H. Knölker,et al.  Iron catalysis in organic synthesis. , 2015, Chemical reviews.

[28]  W. Goddard,et al.  Proton or Metal? The H/D Exchange of Arenes in Acidic Solvents , 2015 .

[29]  W. Goddard,et al.  Rhodium bis(quinolinyl)benzene complexes for methane activation and functionalization. , 2015, Chemistry.

[30]  D. MacMillan,et al.  Merging Photoredox and Nickel Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Vinyl Halides , 2014, Journal of the American Chemical Society.

[31]  W. Goddard,et al.  DFT Virtual Screening Identifies Rhodium−Amidinate Complexes As Potential Homogeneous Catalysts for Methane-to-Methanol Oxidation , 2014 .

[32]  T. Cundari,et al.  Reductive Functionalization of a Rhodium(III)–Methyl Bond in Acidic Media: Key Step in the Electrophilic Functionalization of Methane , 2014 .

[33]  W. Goddard,et al.  Long-range C-H bond activation by Rh(III)-carboxylates. , 2014, Journal of the American Chemical Society.

[34]  J. Groves,et al.  Selective CH functionalization of methane, ethane, and propane by a perfluoroarene iodine(III) complex. , 2014, Angewandte Chemie.

[35]  O. Planas,et al.  Structural modeling of iron halogenases: synthesis and reactivity of halide-iron(IV)-oxo compounds. , 2014, Chemical communications.

[36]  G. Molander,et al.  Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis , 2014, Science.

[37]  C. Pitts,et al.  Direct, catalytic monofluorination of sp³ C-H bonds: a radical-based mechanism with ionic selectivity. , 2014, Journal of the American Chemical Society.

[38]  J. Groves,et al.  Selective monooxidation of light alkanes using chloride and iodate. , 2014, Journal of the American Chemical Society.

[39]  J. Groves,et al.  Reductive functionalization of a rhodium(III)-methyl bond by electronic modification of the supporting ligand. , 2014, Dalton transactions.

[40]  J. Groves,et al.  Late stage benzylic C-H fluorination with [¹⁸F]fluoride for PET imaging. , 2014, Journal of the American Chemical Society.

[41]  Chuo Chen,et al.  Visible light-promoted metal-free C-H activation: diarylketone-catalyzed selective benzylic mono- and difluorination. , 2013, Journal of the American Chemical Society.

[42]  W. Goddard,et al.  Using reduced catalysts for oxidation reactions: mechanistic studies of the "Periana-Catalytica" system for CH4 oxidation. , 2013, Journal of the American Chemical Society.

[43]  M. Sanford,et al.  Effect of Solvent and Ancillary Ligands on the Catalytic H/D Exchange Reactivity of Cp*IrIII(L) Complexes , 2013 .

[44]  D. MacMillan,et al.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. , 2013, Chemical reviews.

[45]  M. Inoue,et al.  Metal-free fluorination of C(sp3)-H bonds using a catalytic N-oxyl radical. , 2013, Organic letters.

[46]  Dariusz Matosiuk,et al.  Click chemistry for drug development and diverse chemical-biology applications. , 2013, Chemical reviews.

[47]  D. Mindiola,et al.  Methane: a new frontier in organometallic chemistry , 2012 .

[48]  David C. Miller,et al.  A polycomponent metal-catalyzed aliphatic, allylic, and benzylic fluorination. , 2012, Angewandte Chemie.

[49]  William A. Goddard,et al.  Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin , 2012, Science.

[50]  M. Sanford,et al.  Rh(III) Pyridinium Substituted Bipyridine Complexes as Catalysts for Arene H/D Exchange , 2012, Topics in Catalysis.

[51]  T. Gunnoe,et al.  Theory of late-transition-metal alkyl and heteroatom bonding: analysis of Pt, Ru, Ir, and Rh complexes. , 2012, Inorganic chemistry.

[52]  M. Sanford,et al.  Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed trifluoromethylation of boronic acids with CF3I. , 2012, Journal of the American Chemical Society.

[53]  R. Periana,et al.  Designing catalysts for functionalization of unactivated C-H bonds based on the CH activation reaction. , 2012, Accounts of chemical research.

[54]  W. Goddard,et al.  The para-substituent effect and pH-dependence of the organometallic Baeyer-Villiger oxidation of rhenium-carbon bonds. , 2012, Dalton transactions.

[55]  V. Gouverneur,et al.  Transition metal catalysis and nucleophilic fluorination. , 2012, Chemical communications.

[56]  Pierre Kennepohl,et al.  Fluorine transfer to alkyl radicals. , 2012, Journal of the American Chemical Society.

[57]  Sara K. Buzak,et al.  Catalytic Arene H/D Exchange with Novel Rhodium and Iridium Complexes , 2012 .

[58]  T. Cundari,et al.  Carbon-oxygen bond formation via organometallic Baeyer-Villiger transformations: a computational study on the impact of metal identity. , 2012, Journal of the American Chemical Society.

[59]  T. Ritter,et al.  Catalysis for fluorination and trifluoromethylation , 2011, Nature.

[60]  W. Goddard,et al.  Functionalization of rhenium aryl bonds by O-atom transfer , 2011 .

[61]  C. Che,et al.  Selective functionalisation of saturated C-H bonds with metalloporphyrin catalysts. , 2011, Chemical Society reviews.

[62]  W. Goddard,et al.  Chemistry in the Center for Catalytic Hydrocarbon Functionalization: An Energy Frontier Research Center , 2011 .

[63]  T. Gunnoe,et al.  Catalytic oxy-functionalization of methane and other hydrocarbons: fundamental advancements and new strategies. , 2011, ChemSusChem.

[64]  W. Goddard,et al.  Rhodium complexes bearing tetradentate diamine-bis(phenolate) ligands. , 2011, Dalton transactions.

[65]  W. Goddard,et al.  Ligand Lone-Pair Influence on Hydrocarbon C-H Activation. A Computational Perspective , 2010 .

[66]  W. Goddard,et al.  Acceleration of nucleophilic CH activation by strongly basic solvents. , 2010, Journal of the American Chemical Society.

[67]  J. Groves,et al.  Manganese porphyrins catalyze selective C-H bond halogenations. , 2010, Journal of the American Chemical Society.

[68]  M. Sanford,et al.  Platinum and palladium complexes containing cationic ligands as catalysts for arene H/D exchange and oxidation. , 2010, Angewandte Chemie.

[69]  Melanie S Sanford,et al.  Palladium-catalyzed ligand-directed C-H functionalization reactions. , 2010, Chemical reviews.

[70]  J. Ellman,et al.  Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation. , 2010, Chemical reviews.

[71]  B. Michalkiewicz,et al.  Kinetic study on catalytic methane esterification in oleum catalyzed by iodine , 2009 .

[72]  W. Goddard,et al.  Product protection, the key to developing high performance methane selective oxidation catalysts. , 2009, Journal of the American Chemical Society.

[73]  C. Walsh,et al.  Substrate positioning controls the partition between halogenation and hydroxylation in the aliphatic halogenase, SyrB2 , 2009, Proceedings of the National Academy of Sciences.

[74]  M. Sanford,et al.  Quantitative Assay for the Direct Comparison of Platinum Catalysts in Benzene H/D Exchange , 2009 .

[75]  K. I. Goldberg,et al.  C−H Bond Activation by Rhodium(I) Phenoxide and Acetate Complexes: Mechanism of H−D Exchange between Arenes and Water , 2008 .

[76]  David O'Hagan,et al.  Understanding organofluorine chemistry. An introduction to the C-F bond. , 2008, Chemical Society reviews.

[77]  J. Lercher,et al.  Methyl chloride production from methane over lanthanum-based catalysts. , 2007, Journal of the American Chemical Society.

[78]  M. Tomaszewska,et al.  Preliminary investigation of low pressure membrane distillation of methyl bisulphate from its solutions in fuming sulphuric acid combined with hydrolysis to methanol , 2006 .

[79]  A. Bueno,et al.  Practical synthesis of aromatic ethers by SNAr of fluorobenzenes with alkoxides , 2006 .

[80]  Armando Carlone,et al.  tert-Butyl Ethers: Renaissance of an Alcohol Protecting Group. Facile Cleavage with Cerium(III) Chloride/Sodium Iodide , 2006 .

[81]  W. Jones On the nature of carbon-hydrogen bond activation at rhodium and related reactions. , 2005, Inorganic chemistry.

[82]  R. Periana,et al.  Perspectives on some challenges and approaches for developing the next generation of selective, low temperature, oxidation catalysts for alkane hydroxylation based on the CH activation reaction , 2004 .

[83]  W. Goddard,et al.  Selective oxidation of methane to methanol catalyzed, with C-H activation, by homogeneous, cationic gold. , 2004, Angewandte Chemie.

[84]  Yimin Zhu,et al.  Iodine as catalyst for the direct oxidation of methane to methyl sulfates in oleum , 2004 .

[85]  R. Periana,et al.  Catalytic, Oxidative Condensation of CH4 to CH3COOH in One Step via CH Activation , 2003, Science.

[86]  S. Blanksby,et al.  Bond dissociation energies of organic molecules. , 2003, Accounts of chemical research.

[87]  R. Periana,et al.  High yield conversion of methane to methyl bisulfate catalyzed by iodine cations. , 2002, Chemical communications.

[88]  J. Bercaw,et al.  Understanding and exploiting C–H bond activation , 2002, Nature.

[89]  Hartwig,et al.  Thermal, catalytic, regiospecific functionalization of alkanes , 2000, Science.

[90]  J. Bercaw,et al.  Homogeneous Oxidation of Alkanes by Electrophilic Late Transition Metals. , 1998, Angewandte Chemie.

[91]  R. Periana,et al.  Platinum catalysts for the high-yield oxidation of methane to a methanol derivative , 1998, Science.

[92]  G. B. Shul’pin,et al.  ACTIVATION OF C-H BONDS BY METAL COMPLEXES , 1997 .

[93]  J. Espenson,et al.  Organic Reactions Catalyzed by Methylrhenium Trioxide: Reactions of Ethyl Diazoacetate and Organic Azides , 1996 .

[94]  S. Mezyk,et al.  Arrhenius Parameter Determination for the Reaction of Methyl Radicals with Iodine Species in Aqueous Solution , 1996 .

[95]  Robert H. Crabtree,et al.  Aspects of Methane Chemistry , 1995 .

[96]  R. Bergman,et al.  Selective Intermolecular Carbon-Hydrogen Bond Activation by Synthetic Metal Complexes in Homogeneous Solution , 1995 .

[97]  L. Que,et al.  Alkane functionalization at nonheme iron centers. Stoichiometric transfer of metal-bound ligands to alkane , 1993 .

[98]  R. Periana,et al.  A Mercury-Catalyzed, High-Yield System for the Oxidation of Methane to Methanol , 1993, Science.

[99]  J. Cowfer,et al.  Oxychlorination of ethylene , 1986 .

[100]  T. Henly,et al.  Catalytic replacement of unactivated alkane carbon-hydrogen bonds with carbon-X bonds (X = nitrogen, oxygen, chlorine, bromine, or iodine). Coupling of intermolecular hydrocarbon activation by MnIIITPPX complexes with phase-transfer catalysis , 1983 .

[101]  Juan C. Scaiano,et al.  Rate constants for the reactions of free radicals with oxygen in solution , 1983 .

[102]  R. Haushalter,et al.  Hydrocarbon Oxidations with Oxometalloporphinates. Isolation and Reactions of a (Porphinato)manganese(V) Complex , 1981 .

[103]  J. Buddrus,et al.  Selective Oxidation of Alkanes and Ethers with Iodine Tris(trifluoroacetate) , 1976 .

[104]  J. Kochi Electron-transfer mechanisms for organometallic intermediates in catalytic reactions , 1974 .

[105]  J. Kochi,et al.  I. Ligand transfer of halides (chloride, bromide, iodide) and pseudohalides (thiocyanate, azide, cyanide) from copper(II) to alkyl radicals , 1971 .

[106]  J. Kochi Mechanisms of Organic Oxidation and Reduction by Metal Complexes , 1967, Science.

[107]  H. Williams,et al.  Some Reactions of Adamantane and Adamantane Derivatives , 1961 .

[108]  Joseph F. Bunnett,et al.  Aromatic Nucleophilic Substitution Reactions. , 1951 .

[109]  G. Egloff,et al.  The Halogenation of the Paraffin Hydrocarbons. , 1931 .

[110]  W. Goddard,et al.  Electrophilic Rh-I catalysts for arene H/D exchange in acidic media: Evidence for an electrophilic aromatic substitution mechanism , 2017 .

[111]  W. Goddard,et al.  Arene C–H activation using Rh( i ) catalysts supported by bidentate nitrogen chelates , 2015 .

[112]  Pan Xu,et al.  When C-H bond functionalization meets visible-light photoredox catalysis , 2014 .

[113]  P. Pérez Alkane C-H Activation by Single-Site Metal Catalysis , 2012 .

[114]  M. Curini,et al.  An Eco-Sustainable Erbium(III)Triflate Catalyzed Formation and Cleavage of tert-ButylEthers , 2011 .

[115]  R. Crabtree Alkane C–H activation and functionalization with homogeneous transition metal catalysts: a century of progress—a new millennium in prospect , 2001 .

[116]  B. Saville,et al.  The trapping of carbon radicals. The competition of oxygen and iodine for the 1,1-diphenylethyl radical , 1975 .