Kinetic Probes of the Origin of Activity in MOF-Based C–H Oxidation Catalysis

Sur, Aishanee; Jernigan, Nicholas B.; Powers, David C.

doi:10.1021/acscatal.1c05415

Kinetic Probes of the Origin of Activity in MOF-Based C–H Oxidation Catalysis

Journal Article · 14 March 2022 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.1c05415· OSTI ID:1978308

Sur, Aishanee ^[1]; Jernigan, Nicholas B. ^[1]; ^[1]

Department of Chemistry, Texas A&M University, College Station, Texas 77843, United States

Not provided.

Research Organization:: Texas A & M Univ., College Station, TX (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0018977

OSTI ID:: 1978308

Journal Information:: ACS Catalysis, Vol. 12, Issue 7; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

References (69)

Sustainability in Catalytic Oxidation: An Alternative Approach or a Structural Evolution? Cavani, Fabrizio; Teles, Joaquim Henrique ChemSusChem, Vol. 2, Issue 6 https://doi.org/10.1002/cssc.200900020	journal	June 2009
Metal–organic framework materials as catalysts Lee, JeongYong; Farha, Omar K.; Roberts, John Chemical Society Reviews, Vol. 38, Issue 5, p. 1450-1459 https://doi.org/10.1039/b807080f	journal	January 2009
Metal-Organic Frameworks as Selective or Chiral Oxidation Catalysts Leus, Karen; Liu, Ying-Ya; Van Der Voort, Pascal Catalysis Reviews, Vol. 56, Issue 1 https://doi.org/10.1080/01614940.2014.864145	journal	January 2014
State of the Art and Prospects in Metal–Organic Framework (MOF)-Based and MOF-Derived Nanocatalysis Wang, Qi; Astruc, Didier Chemical Reviews, Vol. 120, Issue 2 https://doi.org/10.1021/acs.chemrev.9b00223	journal	June 2019
Applications of metal–organic frameworks in heterogeneous supramolecular catalysis Liu, Jiewei; Chen, Lianfen; Cui, Hao Chemical Society Reviews, Vol. 43, Issue 16, p. 6011-6061 https://doi.org/10.1039/C4CS00094C	journal	January 2014
Engineering Metal Organic Frameworks for Heterogeneous Catalysis Corma, A.; García, H.; Llabrés i Xamena, F. X. Chemical Reviews, Vol. 110, Issue 8, p. 4606-4655 https://doi.org/10.1021/cr9003924	journal	August 2010
Metal–organic frameworks: versatile heterogeneous catalysts for efficient catalytic organic transformations Chughtai, Adeel H.; Ahmad, Nazir; Younus, Hussein A. Chemical Society Reviews, Vol. 44, Issue 19 https://doi.org/10.1039/C4CS00395K	journal	January 2015
Metal Organic Framework Catalysis: Quo vadis ? Gascon, Jorge; Corma, Avelino; Kapteijn, Freek ACS Catalysis, Vol. 4, Issue 2, p. 361-378 https://doi.org/10.1021/cs400959k	journal	December 2013
Biomimetic catalysis of metal–organic frameworks Chen, Yao; Ma, Shengqian Dalton Transactions, Vol. 45, Issue 24 https://doi.org/10.1039/C6DT00325G	journal	January 2016
Artificial Metalloenzymes: Recent Developments and Innovations in Bioinorganic Catalysis Thompson, Zechariah; Cowan, James Allan Small, Vol. 16, Issue 27 https://doi.org/10.1002/smll.202000392	journal	May 2020
Bioinspired chemistry at MOF secondary building units Bour, James R.; Wright, Ashley M.; He, Xin Chemical Science, Vol. 11, Issue 7 https://doi.org/10.1039/C9SC06418D	journal	January 2020
Designed fabrication of biomimetic metal–organic frameworks for catalytic applications Chen, Kai; Wu, Chuan-De Coordination Chemistry Reviews, Vol. 378 https://doi.org/10.1016/j.ccr.2018.01.016	journal	January 2019
Metal–organic and covalent organic frameworks as single-site catalysts Rogge, S. M. J.; Bavykina, A.; Hajek, J. Chemical Society Reviews, Vol. 46, Issue 11 https://doi.org/10.1039/C7CS00033B	journal	January 2017
In Operando Analysis of Diffusion in Porous Metal‐Organic Framework Catalysts Gao, Wen‐Yang; Cardenal, Ashley D.; Wang, Chen‐Hao Chemistry – A European Journal, Vol. 25, Issue 14 https://doi.org/10.1002/chem.201804490	journal	December 2018
A More General Approach to Distinguishing "Homogeneous" from "Heterogeneous" Catalysis: Discovery of Polyoxoanion- and Bu4N+-Stabilized, Isolable and Redissolvable, High-Reactivity Ir.apprx.190-450 Nanocluster Catalysts Lin, Yin; Finke, Richard G. Inorganic Chemistry, Vol. 33, Issue 22 https://doi.org/10.1021/ic00100a012	journal	October 1994
Heterogeneous Catalysts for Liquid-Phase Oxidations: Philosophers' Stones or Trojan Horses? Sheldon, Roger A.; Wallau, Martin; Arends, Isabel W. C. E. Accounts of Chemical Research, Vol. 31, Issue 8 https://doi.org/10.1021/ar9700163	journal	August 1998
A review of the problem of distinguishing true homogeneous catalysis from soluble or other metal-particle heterogeneous catalysis under reducing conditions Widegren, Jason A.; Finke, Richard G. Journal of Molecular Catalysis A: Chemical, Vol. 198, Issue 1-2 https://doi.org/10.1016/S1381-1169(02)00728-8	journal	May 2003
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
Distinguishing Homogeneous from Heterogeneous Water Oxidation Catalysis when Beginning with Polyoxometalates Stracke, Jordan J.; Finke, Richard G. ACS Catalysis, Vol. 4, Issue 3 https://doi.org/10.1021/cs4011716	journal	January 2014
Homogeneous vs. heterogeneous: mechanistic insights into iron group metal-catalyzed reductions from poisoning experiments Gärtner, Dominik; Sandl, Sebastian; Jacobi von Wangelin, Axel Catalysis Science & Technology, Vol. 10, Issue 11 https://doi.org/10.1039/D0CY00644K	journal	January 2020
Solar fuels generation and molecular systems: is it homogeneous or heterogeneous catalysis? Artero, Vincent; Fontecave, Marc Chem. Soc. Rev., Vol. 42, Issue 6 https://doi.org/10.1039/C2CS35334B	journal	January 2013
On the Nature of the Active Species in Palladium Catalyzed Mizoroki–Heck and Suzuki–Miyaura Couplings – Homogeneous or Heterogeneous Catalysis, A Critical Review Phan, Nam T. S.; Van Der Sluys, Matthew; Jones, Christopher W. Advanced Synthesis & Catalysis, Vol. 348, Issue 6 https://doi.org/10.1002/adsc.200505473	journal	April 2006
Pd nanoparticles for C–C coupling reactions Balanta, Angelica; Godard, Cyril; Claver, Carmen Chemical Society Reviews, Vol. 40, Issue 10 https://doi.org/10.1039/c1cs15195a	journal	January 2011
“Homeopathic” Palladium Nanoparticle Catalysis of Cross Carbon–Carbon Coupling Reactions Deraedt, Christophe; Astruc, Didier Accounts of Chemical Research, Vol. 47, Issue 2 https://doi.org/10.1021/ar400168s	journal	November 2013
Über den Einfluß von Fremdstoffen auf die Aktivität der Katalysatoren. IV.: Versuche mit Palladiumhydrosol in Gegenwart von Quecksilber und Quecksilberoxyd Paal, C.; Hartmann, Wilhelm Berichte der deutschen chemischen Gesellschaft, Vol. 51, Issue 1 https://doi.org/10.1002/cber.19180510186	journal	January 1918
When Applying the Mercury Poisoning Test to Palladacycle-Catalyzed Reactions, One Should Not Consider the Common Misconception of Mercury(0) Selectivity Gorunova, Olga N.; Novitskiy, Ivan M.; Grishin, Yuri K. Organometallics, Vol. 37, Issue 17 https://doi.org/10.1021/acs.organomet.8b00363	journal	July 2018
Mass transfer test and maximum rate determination during liquid-phase hydrogenations Notheisz, Ferenc; Zsigmond, A´gnes; Barto´k, Miha´ly Applied Catalysis A: General, Vol. 120, Issue 1 https://doi.org/10.1016/0926-860X(94)80336-6	journal	December 1994
Nanoclusters in Catalysis: A Comparison of CS ₂ Catalyst Poisoning of Polyoxoanion- and Tetrabutylammonium-Stabilized 40 ± 6 Å Rh(0) Nanoclusters to 5 Rh/Al ₂ O ₃ , Including an Analysis of the Literature Related to the CS ₂ to Metal Stoichiometry Issue Hornstein, Brooks J.; Aiken, John D.; Finke, Richard G. Inorganic Chemistry, Vol. 41, Issue 6 https://doi.org/10.1021/ic010920y	journal	March 2002
Is It Homogeneous or Heterogeneous Catalysis Derived from [RhCpCl ₂ ] ₂ ? In Operando* XAFS, Kinetic, and Crucial Kinetic Poisoning Evidence for Subnanometer Rh ₄ Cluster-Based Benzene Hydrogenation Catalysis Bayram, Ercan; Linehan, John C.; Fulton, John L. Journal of the American Chemical Society, Vol. 133, Issue 46 https://doi.org/10.1021/ja2073438	journal	November 2011
Mononuclear Zeolite-Supported Iridium: Kinetic, Spectroscopic, Electron Microscopic, and Size-Selective Poisoning Evidence for an Atomically Dispersed True Catalyst at 22 °C Bayram, Ercan; Lu, Jing; Aydin, Ceren ACS Catalysis, Vol. 2, Issue 9 https://doi.org/10.1021/cs300366w	journal	August 2012
Quantitative 1,10-Phenanthroline Catalyst-Poisoning Kinetic Studies of Rh(0) Nanoparticle and Rh ₄ Cluster Benzene Hydrogenation Catalysts: Estimates of the Poison K _association Binding Constants, of the Equivalents of Poison Bound and of the Number of Catalytically Active Sites for Each Catalyst Bayram, Ercan; Finke, Richard G. ACS Catalysis, Vol. 2, Issue 9 https://doi.org/10.1021/cs300330c	journal	August 2012
Regulation of Iron-Catalyzed Olefin Hydroboration by Ligand Modifications at a Remote Site Tseng, Kuei-Nin T.; Kampf, Jeff W.; Szymczak, Nathaniel K. ACS Catalysis, Vol. 5, Issue 1 https://doi.org/10.1021/cs501820w	journal	November 2014
Silica and polymer-tethered Pd?SCS-pincer complexes: evidence for precatalyst decomposition to form soluble catalytic species in Mizoroki?Heck chemistry Yu, K. Journal of Catalysis, Vol. 226, Issue 1 https://doi.org/10.1016/j.jcat.2004.05.015	journal	August 2004
Leached nickel promotes catalysis using supported Ni(II) complex precatalysts in Kumada-Corriu reactions Richardson, John M.; Jones, Christopher W. Journal of Molecular Catalysis A: Chemical, Vol. 297, Issue 2 https://doi.org/10.1016/j.molcata.2008.09.021	journal	January 2009
Aerobic Dehydrogenation of Cyclohexanone to Phenol Catalyzed by Pd(TFA) ₂ /2-Dimethylaminopyridine: Evidence for the Role of Pd Nanoparticles Pun, Doris; Diao, Tianning; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 135, Issue 22 https://doi.org/10.1021/ja403165u	journal	May 2013
Three-phase test for reactive intermediates. Cyclobutadiene Rebek, J.; Gavina, F. Journal of the American Chemical Society, Vol. 96, Issue 22 https://doi.org/10.1021/ja00829a056	journal	October 1974
Three-phase test for reaction intermediates. Nucleophilic catalysis and elimination reactions Rebek, Julius; Brown, David; Zimmerman, Stephen Journal of the American Chemical Society, Vol. 97, Issue 2 https://doi.org/10.1021/ja00835a057	journal	January 1975
Are Heterogeneous Catalysts Precursors to Homogeneous Catalysts? Davies, Ian W.; Matty, Louis; Hughes, David L. Journal of the American Chemical Society, Vol. 123, Issue 41 https://doi.org/10.1021/ja016877v	journal	October 2001
Transition Metal Nanocluster Formation Kinetic and Mechanistic Studies. A New Mechanism When Hydrogen Is the Reductant: Slow, Continuous Nucleation and Fast Autocatalytic Surface Growth Watzky, Murielle A.; Finke, Richard G. Journal of the American Chemical Society, Vol. 119, Issue 43 https://doi.org/10.1021/ja9705102	journal	October 1997
Is it homogeneous Pt(II) or heterogeneous Pt(0)n catalysis? Evidence that Pt(1,5-COD)Cl2 and Pt(1,5-COD)(CH3)2 plus H2 form heterogeneous, nanocluster plus bulk-metal Pt(0) hydrogenation catalysts Finney, Eric E.; Finke, Richard G. Inorganica Chimica Acta, Vol. 359, Issue 9 https://doi.org/10.1016/j.ica.2005.11.023	journal	June 2006
Iron-Catalyzed Cross-Coupling of Alkenyl Acetates Gärtner, Dominik; Stein, André Luiz; Grupe, Sabine Angewandte Chemie International Edition, Vol. 54, Issue 36 https://doi.org/10.1002/anie.201504524	journal	July 2015
Probing Substrate Diffusion in Interstitial MOF Chemistry with Kinetic Isotope Effects Wang, Chen-Hao; Das, Anuvab; Gao, Wen-Yang Angewandte Chemie International Edition, Vol. 57, Issue 14 https://doi.org/10.1002/anie.201713244	journal	March 2018
Measuring and Modulating Substrate Confinement during Nitrogen-Atom Transfer in a Ru ₂ -Based Metal-Organic Framework Wang, Chen-Hao; Gao, Wen-Yang; Powers, David C. Journal of the American Chemical Society, Vol. 141, Issue 49 https://doi.org/10.1021/jacs.9b09620	journal	November 2019
On the Interpretation of Deuterium Kinetic Isotope Effects in CH Bond Functionalizations by Transition-Metal Complexes Simmons, Eric M.; Hartwig, John F. Angewandte Chemie International Edition, Vol. 51, Issue 13 https://doi.org/10.1002/anie.201107334	journal	March 2012
Rational Construction of an Artificial Binuclear Copper Monooxygenase in a Metal–Organic Framework Feng, Xuanyu; Song, Yang; Chen, Justin S. Journal of the American Chemical Society, Vol. 143, Issue 2 https://doi.org/10.1021/jacs.0c11920	journal	January 2021
Structural and Mechanistic Insights into Methane Oxidation by Particulate Methane Monooxygenase Balasubramanian, Ramakrishnan; Rosenzweig, Amy C. Accounts of Chemical Research, Vol. 40, Issue 7 https://doi.org/10.1021/ar700004s	journal	July 2007
Hydroxylation/oxidation of benzene over Cu-ZSM-5 systems: Optimization of the one-step route to phenol Kubacka, A.; Wang, Z.; Sulikowski, B. Journal of Catalysis, Vol. 250, Issue 1 https://doi.org/10.1016/j.jcat.2007.05.017	journal	August 2007
Oxidase catalysis via aerobically generated hypervalent iodine intermediates Maity, Asim; Hyun, Sung-Min; Powers, David C. Nature Chemistry, Vol. 10, Issue 2 https://doi.org/10.1038/nchem.2873	journal	October 2017
Oxidation Catalysis by an Aerobically Generated Dess-Martin Periodinane Analogue Maity, Asim; Hyun, Sung-Min; Wortman, Alan K. Angewandte Chemie International Edition, Vol. 57, Issue 24 https://doi.org/10.1002/anie.201804159	journal	May 2018
The Role of Iodanyl Radicals as Critical Chain Carriers in Aerobic Hypervalent Iodine Chemistry Hyun, Sung-Min; Yuan, Mingbin; Maity, Asim Chem, Vol. 5, Issue 9 https://doi.org/10.1016/j.chempr.2019.06.006	journal	September 2019
Iodoarene-catalyzed oxidative transformations using molecular oxygen Miyamoto, K.; Yamashita, J.; Narita, S. Chemical Communications, Vol. 53, Issue 70 https://doi.org/10.1039/C7CC05160C	journal	January 2017
A mechanistic study of the liquid phase autoxidation of nonan-5-one Hammond, Christopher J.; Lindsay Smith, John R.; Nagatomi, Eiji New Journal of Chemistry, Vol. 30, Issue 5 https://doi.org/10.1039/b518114c	journal	January 2006
Aerobic Direct C(sp2)-H Hydroxylation of 2-Arylpyridines by Palladium Catalysis Induced with Aldehyde Auto-Oxidation Das, Prasenjit; Saha, Debajyoti; Saha, Dibyajyoti ACS Catalysis, Vol. 6, Issue 9 https://doi.org/10.1021/acscatal.6b01539	journal	August 2016
A practical synthesis of α-aminophosphonic acids. Genêt, J. P.; Uziel, J.; Port, M. Tetrahedron Letters, Vol. 33, Issue 1 https://doi.org/10.1016/S0040-4039(00)77677-5	journal	January 1992
Aldehyde/olefin cooxidations: Parallel epoxidation pathways and concerted decomposition of the peroxyacyl-olefin adduct Lassila, Kevin R.; Waller, Francis J.; Werkheiser, Steven E. Tetrahedron Letters, Vol. 35, Issue 44 https://doi.org/10.1016/0040-4039(94)88247-9	journal	October 1994
Mechanistic Studies on the Mukaiyama Epoxidation Wentzel, Bastienne B.; Alsters, Paul L.; Feiters, Martinus C. The Journal of Organic Chemistry, Vol. 69, Issue 10 https://doi.org/10.1021/jo030345a	journal	May 2004
Mechanism of Oxygen Transfer in the Epoxidation of an Olefin by Molecular Oxygen in the Presence of an Aldehyde Jarboe, Stephen G.; Beak, Peter Organic Letters, Vol. 2, Issue 3 https://doi.org/10.1021/ol991304x	journal	January 2000
Peroxy radicals Ingold, Keith U. Accounts of Chemical Research, Vol. 2, Issue 1 https://doi.org/10.1021/ar50013a001	journal	January 1969
Absolute rate constants for hydrocarbon oxidation. VIII. The reactions of cumylperoxy radicals Howard, J. A.; Ingold, K. U.; Symonds, M. Canadian Journal of Chemistry, Vol. 46, Issue 6 https://doi.org/10.1139/v68-165	journal	March 1968
Competition H(D) Kinetic Isotope Effects in the Autoxidation of Hydrocarbons Muchalski, Hubert; Levonyak, Alexander J.; Xu, Libin Journal of the American Chemical Society, Vol. 137, Issue 1 https://doi.org/10.1021/ja511434j	journal	December 2014
The role of catalysts in the air oxidation of aliphatic aldehydes Larkin, Donald R. The Journal of Organic Chemistry, Vol. 55, Issue 5 https://doi.org/10.1021/jo00292a035	journal	March 1990
Factors Affecting the Selectivity of Air Oxidation Of 2-Ethyhexanal, an α-Branched Aliphatic Aldehyde Lehtinen, Christel; Brunow, Gösta Organic Process Research & Development, Vol. 4, Issue 6 https://doi.org/10.1021/op000045k	journal	October 2000
Mechanistic Study on Gold-Catalyzed Highly Selective Hydroamination of Alkylidenecyclopropanes Wang, Chen; Ren, Xiao-Rong; Qi, Chen-Ze The Journal of Organic Chemistry, Vol. 81, Issue 17 https://doi.org/10.1021/acs.joc.6b00726	journal	August 2016
Regio- and Diastereoselective Iron-Catalyzed [4+4]-Cycloaddition of 1,3-Dienes Kennedy, C. Rose; Zhong, Hongyu; Macaulay, Rachel L. Journal of the American Chemical Society, Vol. 141, Issue 21 https://doi.org/10.1021/jacs.9b02443	journal	May 2019
Diastereoselective olefin amidoacylation via photoredox PCET/nickel-dual catalysis: reaction scope and mechanistic insights Zheng, Shuai; Zhang, Shuo-Qing; Saeednia, Borna Chemical Science, Vol. 11, Issue 16 https://doi.org/10.1039/D0SC01459A	journal	January 2020
Co-oxidative epoxidation of cyclohexene with molecular oxygen, isobutyraldehyde reductant, and the polyoxoanion-supported catalyst precursor [(n-C4H9)4N]5Na3[(1,5-COD)Ir · P2W15Nb3O62]. The importance of key control experiments including omitting the catalyst and adding radical-chain initiators Mizuno, Noritaka; Weiner, Heiko; Finke, Richard G. Journal of Molecular Catalysis A: Chemical, Vol. 114, Issue 1-3 https://doi.org/10.1016/S1381-1169(96)00301-9	journal	December 1996
Metal Complex-Catalyzed Epoxidation of Olefins by Dioxygen with Co-Oxidation of Aldehydes. A Mechanistic Study Nam, Wonwoo; Kim, Hyo Jin; Kim, Seong Hoon Inorganic Chemistry, Vol. 35, Issue 4 https://doi.org/10.1021/ic950782a	journal	January 1996
Oxidation of ethane to ethanol by N2O in a metal–organic framework with coordinatively unsaturated iron(II) sites Xiao, Dianne J.; Bloch, Eric D.; Mason, Jarad A. Nature Chemistry, Vol. 6, Issue 7 https://doi.org/10.1038/nchem.1956	journal	May 2014
Mechanism of Oxidation of Ethane to Ethanol at Iron(IV)–Oxo Sites in Magnesium-Diluted Fe ₂ (dobdc) Verma, Pragya; Vogiatzis, Konstantinos D.; Planas, Nora Journal of the American Chemical Society, Vol. 137, Issue 17 https://doi.org/10.1021/jacs.5b00382	journal	April 2015

Similar Records

Kinetic Probes of the Origin of Activity in MOF-Based C–H Oxidation Catalysis

Journal Article · 2022 · ACS Catalysis · OSTI ID:2433870

Sur, Aishanee; Jernigan, Nicholas B.; Powers, David C.

Selectivity of Chemisorbed Oxygen in C–H Bond Activation and CO Oxidation and Kinetic Consequences for CH₄–O₂ Catalysis on Pt and Rh Clusters

Journal Article · 2011 · Journal of Catalysis, 283(1):10-24 · OSTI ID:1053389

Chin, Ya-Huei; Buda, Corneliu; Neurock, Matthew; +1 more

C–H Bond Activation on Bimetallic Two-Atom Co-M Oxide Clusters Deposited on Zr-Based MOF Nodes: Effects of Doping at the Molecular Level

Journal Article · 2018 · ACS Catalysis · OSTI ID:1470254

Simons, Matthew C.; Ortuño, Manuel A.; Bernales, Varinia; +4 more

Related Subjects

Chemistry

Kinetic Probes of the Origin of Activity in MOF-Based C–H Oxidation Catalysis

Citation Formats

References (69)

Similar Records

Related Subjects