Partial oxidation of light alkanes by periodate and chloride salts

Kalman, Steven E.; Munz, Dominik; Fortman, George C.; Boaz, Nicholas C.; Groves, John T; Gunnoe, T. Brent

doi:10.1039/c5dt00558b

Title: Partial oxidation of light alkanes by periodate and chloride salts

Journal Article · Thu Jan 01 00:00:00 EST 2015 · Dalton Trans.

DOI:https://doi.org/10.1039/c5dt00558b· OSTI ID:1210867

Kalman, Steven E.; Munz, Dominik; Fortman, George C.; Boaz, Nicholas C.; Groves, John T; Gunnoe, T. Brent

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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Catalytic Hydrocarbon Functionalization (CCHF)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

DOE Contract Number:: SC0001298

OSTI ID:: 1210867

Journal Information:: Dalton Trans., Vol. 44; Related Information: CCHF partners with University of Virginia (lead); Brigham Young University; California Institute of Technology; Colorado School of Mines; University of Maryland; University of North Carolina, Chapel Hill; University of North Texas; Princeton University; The Scripps Research Institute; Yale University

Country of Publication:: United States

Language:: English

References (44)

Catalytic Oxy-Functionalization of Methane and Other Hydrocarbons: Fundamental Advancements and New Strategies Webb, Joanna R.; Bolaño, Tamara; Gunnoe, T. Brent ChemSusChem, Vol. 4, Issue 1 https://doi.org/10.1002/cssc.201000319	journal	December 2010
Selective alkane oxidation: hot and cold approaches to a hot problem Labinger, Jay A. Journal of Molecular Catalysis A: Chemical, Vol. 220, Issue 1 https://doi.org/10.1016/j.molcata.2004.03.051	journal	September 2004
Homogeneous Organometallic Chemistry of Methane Cavaliere, Vincent N.; Wicker, Benjamin F.; Mindiola, Daniel J. Advances in Organometallic Chemistry, Vol. 60 https://doi.org/10.1016/B978-0-12-396970-5.00001-3	book	January 2012
Homogeneous Oxidation of Alkanes by Electrophilic Late Transition Metals Stahl, Shannon S.; Labinger, Jay A.; Bercaw, John E. Angewandte Chemie International Edition, Vol. 37, Issue 16 https://doi.org/10.1002/(SICI)1521-3773(19980904)37:16<2180::AID-ANIE2180>3.0.CO;2-A	journal	September 1998
Activation of C−H Bonds by Metal Complexes Shilov, Alexander E.; Shul'pin, Georgiy B. Chemical Reviews, Vol. 97, Issue 8 https://doi.org/10.1021/cr9411886	journal	December 1997
Understanding and exploiting C–H bond activation Labinger, Jay A.; Bercaw, John E. Nature, Vol. 417, Issue 6888 https://doi.org/10.1038/417507a	journal	May 2002
Methane as raw material in synthetic chemistry: the final frontier Caballero, Ana; Pérez, Pedro J. Chemical Society Reviews, Vol. 42, Issue 23 https://doi.org/10.1039/c3cs60120j	journal	January 2013
Selective Catalytic Oxidation of CH Bonds with Molecular Oxygen Roduner, Emil; Kaim, Wolfgang; Sarkar, Biprajit ChemCatChem, Vol. 5, Issue 1 https://doi.org/10.1002/cctc.201200266	journal	October 2012
Chemistry with Methane: Concepts Rather than Recipes Schwarz, Helmut Angewandte Chemie International Edition, Vol. 50, Issue 43 https://doi.org/10.1002/anie.201006424	journal	June 2011
C−H Bond Activations by Metal Oxo Compounds Gunay, Ahmet; Theopold, Klaus H. Chemical Reviews, Vol. 110, Issue 2 https://doi.org/10.1021/cr900269x	journal	February 2010
Umpolung of a Metal−Carbon Bond: A Potential Route to Porphyrin-Based Methane Functionalization Catalysts Nelson, Andrew P.; DiMagno, Stephen G. Journal of the American Chemical Society, Vol. 122, Issue 35 https://doi.org/10.1021/ja001380r	journal	September 2000
Catalyst-Controlled Aliphatic C–H Oxidations with a Predictive Model for Site-Selectivity Gormisky, Paul E.; White, M. Christina Journal of the American Chemical Society, Vol. 135, Issue 38 https://doi.org/10.1021/ja407388y	journal	September 2013
Spectroscopic and Theoretical Investigation of a Complex with an [O═Fe ^IV –O–Fe ^IV ═O] Core Related to Methane Monooxygenase Intermediate Q Stoian, Sebastian A.; Xue, Genqiang; Bominaar, Emile L. Journal of the American Chemical Society, Vol. 136, Issue 4 https://doi.org/10.1021/ja411376u	journal	January 2014
Precursor Transformation during Molecular Oxidation Catalysis with Organometallic Iridium Complexes Hintermair, Ulrich; Sheehan, Stafford W.; Parent, Alexander R. Journal of the American Chemical Society, Vol. 135, Issue 29 https://doi.org/10.1021/ja4048762	journal	July 2013
Manganese Porphyrins Catalyze Selective C−H Bond Halogenations Liu, Wei; Groves, John T. Journal of the American Chemical Society, Vol. 132, Issue 37 https://doi.org/10.1021/ja105548x	journal	September 2010
Manganese-Catalyzed Oxidative Benzylic C-H Fluorination by Fluoride Ions Liu, Wei; Groves, John T. Angewandte Chemie International Edition, Vol. 52, Issue 23 https://doi.org/10.1002/anie.201301097	journal	April 2013
Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin Liu, W.; Huang, X.; Cheng, M. -J. Science, Vol. 337, Issue 6100 https://doi.org/10.1126/science.1222327	journal	September 2012
Kinetics and Mechanism of Methane, Methanol, and Dimethyl Ether C−H Activation with Electrophilic Platinum Complexes Owen, Jonathan S.; Labinger, Jay A.; Bercaw, John E. Journal of the American Chemical Society, Vol. 128, Issue 6 https://doi.org/10.1021/ja056387t	journal	February 2006
Direct Observation of a Picosecond Alkane C−H Bond Activation Reaction at Iridium Asbury, John B.; Hang, Kun; Yeston, Jake S. Journal of the American Chemical Society, Vol. 122, Issue 51 https://doi.org/10.1021/ja0028065	journal	December 2000
Resolving Heterogeneity Problems and Impurity Artifacts in Operationally Homogeneous Transition Metal Catalysts Crabtree, Robert H. Chemical Reviews, Vol. 112, Issue 3 https://doi.org/10.1021/cr2002905	journal	October 2011
Homogeneous catalysis in the oxidative functionalization of alkanes in protic media Chepaikin, E. G. Russian Chemical Reviews, Vol. 80, Issue 4 https://doi.org/10.1070/RC2011v080n04ABEH004131	journal	April 2011
Selective Oxidation of Methane to Methanol Catalyzed, with CH Activation, by Homogeneous, Cationic Gold Jones, Cj; Taube, Doug; Ziatdinov, Vadim R. Angewandte Chemie International Edition, Vol. 43, Issue 35 https://doi.org/10.1002/anie.200461055	journal	September 2004
Platinum Catalysts for the High-Yield Oxidation of Methane to a Methanol Derivative Periana, R. A. Science, Vol. 280, Issue 5363 https://doi.org/10.1126/science.280.5363.560	journal	April 1998
Low-temperature, palladium(II)-catalyzed, solution-phase oxidation of methane to methanol derivative Kao, Lien Chung; Hutson, Alan C.; Sen, Ayusman Journal of the American Chemical Society, Vol. 113, Issue 2 https://doi.org/10.1021/ja00002a063	journal	January 1991
Propane Activation by Palladium Complexes with Chelating Bis(NHC) Ligands and Aerobic Cooxidation Munz, Dominik; Strassner, Thomas Angewandte Chemie International Edition, Vol. 53, Issue 9 https://doi.org/10.1002/anie.201309568	journal	January 2014
Cobalt-Catalyzed Oxidation of Methane to Methyl Trifluoroacetate by Dioxygen Strassner, Thomas; Ahrens, Sebastian; Muehlhofer, Michael European Journal of Inorganic Chemistry, Vol. 2013, Issue 21 https://doi.org/10.1002/ejic.201300213	journal	July 2013
Manganese oxide catalyzed methane partial oxidation in trifluoroacetic acid: Catalysis and kinetic analysis Chen, Wensheng; Kocal, Joseph A.; Brandvold, Timothy A. Catalysis Today, Vol. 140, Issue 3-4 https://doi.org/10.1016/j.cattod.2008.10.011	journal	February 2009
Silver(I)-Catalyzed Insertion of Carbene into Alkane C–H Bonds and the Origin of the Special Challenge of Methane Activation Using DFT as a Mechanistic Probe Flores, Jaime A.; Komine, Nobuyuki; Pal, Kuntal ACS Catalysis, Vol. 2, Issue 10 https://doi.org/10.1021/cs300256b	journal	August 2012
Silver-Catalyzed C-C Bond Formation Between Methane and Ethyl Diazoacetate in Supercritical CO2 Caballero, A.; Despagnet-Ayoub, E.; Mar Diaz-Requejo, M. Science, Vol. 332, Issue 6031 https://doi.org/10.1126/science.1204131	journal	May 2011
Main-Group Compounds Selectively Oxidize Mixtures of Methane, Ethane, and Propane to Alcohol Esters Hashiguchi, B. G.; Konnick, M. M.; Bischof, S. M. Science, Vol. 343, Issue 6176, p. 1232-1237 https://doi.org/10.1126/science.1249357	journal	March 2014
Alkane Bromination Revisited: “Reproportionation” in Gas-Phase Methane Bromination Leads to Higher Selectivity for CH ₃ Br at Moderate Temperatures Lorkovic, Ivan M.; Sun, Shouli; Gadewar, Sagar The Journal of Physical Chemistry A, Vol. 110, Issue 28 https://doi.org/10.1021/jp061558h	journal	July 2006
The Selective High-Yield Conversion of Methane Using Iodine-Catalyzed Methane Bromination Ding, Kunlun; Metiu, Horia; Stucky, Galen D. ACS Catalysis, Vol. 3, Issue 3 https://doi.org/10.1021/cs300775m	journal	February 2013
Chemistry of Polyvalent Iodine Zhdankin, Viktor V.; Stang, Peter J. Chemical Reviews, Vol. 108, Issue 12 https://doi.org/10.1021/cr800332c	journal	December 2008
Hypervalent Iodine Goes Catalytic Richardson, Robert D.; Wirth, Thomas Angewandte Chemie International Edition, Vol. 45, Issue 27 https://doi.org/10.1002/anie.200601817	journal	July 2006
Hypervalent Iodine Chemistry in Synthesis: Scope and New Directions Wirth, Thomas Angewandte Chemie International Edition, Vol. 44, Issue 24 https://doi.org/10.1002/anie.200500115	journal	June 2005
New Site-Selective Organoradical Based on Hypervalent Iodine Reagent for Controlled Alkane sp ³ CH Oxidations Dohi, Toshifumi; Kita, Yasuyuki ChemCatChem, Vol. 6, Issue 1 https://doi.org/10.1002/cctc.201300666	journal	September 2013
Site-Selective Oxidation of Unactivated C sp 3H Bonds with Hypervalent Iodine(III) Reagents Moteki, Shin A.; Usui, Asuka; Zhang, Tiexin Angewandte Chemie International Edition, Vol. 52, Issue 33 https://doi.org/10.1002/anie.201304359	journal	July 2013
Iodine Catalyzed Propane Oxidative Dehydrogenation Using Dibromomethane as an Oxidant Ding, Kunlun; Zhang, Aihua; Stucky, Galen D. ACS Catalysis, Vol. 2, Issue 6 https://doi.org/10.1021/cs3001418	journal	April 2012
Selective Oxidation of Alkanes and Ethers with Iodine Tris(trifluoroacetate) Buddrus, Joachim; Plettenberg, Horst Angewandte Chemie International Edition in English, Vol. 15, Issue 7 https://doi.org/10.1002/anie.197604361	journal	July 1976
Kinetic study on catalytic methane esterification in oleum catalyzed by iodine Michalkiewicz, Beata; Jarosińska, Monika; Łukasiewicz, Iwona Chemical Engineering Journal, Vol. 154, Issue 1-3 https://doi.org/10.1016/j.cej.2009.03.046	journal	November 2009
Iodine as catalyst for the direct oxidation of methane to methyl sulfates in oleum Gang, Xiao; Zhu, Yimin; Birch, Henning Applied Catalysis A: General, Vol. 261, Issue 1 https://doi.org/10.1016/j.apcata.2003.10.039	journal	April 2004
High yield conversion of methane to methyl bisulfate catalyzed by iodine cations Periana, Roy A.; Mirinov, Oleg; Taube, Douglas J. Chemical Communications, Issue 20 https://doi.org/10.1039/b205366g	journal	September 2002
Selective CH Functionalization of Methane, Ethane, and Propane by a Perfluoroarene Iodine(III) Complex Konnick, Michael M.; Hashiguchi, Brian G.; Devarajan, Deepa Angewandte Chemie International Edition, Vol. 53, Issue 39, p. 10490-10494 https://doi.org/10.1002/anie.201406185	journal	August 2014
Selective Monooxidation of Light Alkanes Using Chloride and Iodate Fortman, George C.; Boaz, Nicholas C.; Munz, Dominik Journal of the American Chemical Society, Vol. 136, Issue 23 https://doi.org/10.1021/ja502657g	journal	May 2014

Cited By (3)

Selective Photo‐Oxygenation of Light Alkanes Using Iodine Oxides and Chloride Liebov, Nichole S.; Goldberg, Jonathan M.; Boaz, Nicholas C. ChemCatChem, Vol. 11, Issue 20 https://doi.org/10.1002/cctc.201901175	journal	September 2019
Methane conversion into different hydrocarbons or oxygenates: current status and future perspectives in catalyst development and reactor operation Kondratenko, Evgenii V.; Peppel, Tim; Seeburg, Dominik Catalysis Science & Technology, Vol. 7, Issue 2 https://doi.org/10.1039/c6cy01879c	journal	January 2017
Selective benzylic C–H monooxygenation mediated by iodine oxides LaMartina, Kelsey B.; Kuck, Haley K.; Oglesbee, Linda S. Beilstein Journal of Organic Chemistry, Vol. 15 https://doi.org/10.3762/bjoc.15.55	journal	January 2019

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