Chemoselective Hydrogenation with Supported Organoplatinum(IV) Catalyst on Zn(II)-Modified Silica

Camacho-Bunquin, Jeffrey; Ferrandon, Magali; Sohn, Hyuntae; Yang, Dali; Liu, Cong; Ignacio-de Leon, Patricia Anne; Perras, Frédéric A.; Pruski, Marek; Stair, Peter C.; Delferro, Massimiliano

doi:10.1021/jacs.7b11981

Title: Chemoselective Hydrogenation with Supported Organoplatinum(IV) Catalyst on Zn(II)-Modified Silica

Journal Article · Tue Feb 27 04:00:00 UTC 2018 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.7b11981 · OSTI ID:1427735

^[1]; Ferrandon, Magali ^[1]; Sohn, Hyuntae ^[1]; Yang, Dali ^[1];

^[1]; Ignacio-de Leon, Patricia Anne ^[2]; Perras, Frédéric A. ^[3];

^[4]; Stair, Peter C. ^[5];

^[1]

Argonne National Lab. (ANL), Lemont, IL (United States). Chemical Sciences and Engineering Division
Argonne National Lab. (ANL), Lemont, IL (United States). Energy Sciences Division
Ames Lab., Ames, IA (United States)
Ames Lab., Ames, IA (United States); Iowa State Univ., Ames, IA (United States). Department of Chemistry
Argonne National Lab. (ANL), Lemont, IL (United States). Chemical Sciences and Engineering Division ; Northwestern Univ., Evanston, IL (United States). Department of Chemistry

For this research, well-defined organoplatinum(IV) sites were grafted on a Zn(II)-modified SiO₂ support via surface organometallic chemistry in toluene at room temperature. Solid-state spectroscopies including XAS, DRIFTS, DRUV–vis, and solid-state (SS) NMR enhanced by dynamic nuclear polarization (DNP), as well as TPR-H₂ and TEM techniques revealed highly dispersed (methylcyclopentadienyl)methylplatinum(IV) sites on the surface ((MeCp)PtMe/Zn/SiO₂, 1). In addition, computational modeling suggests that the surface reaction of (MeCp)PtMe₃ with Zn(II)-modified SiO₂ support is thermodynamically favorable (ΔG = -12.4 kcal/mol), likely due to the increased acidity of the hydroxyl group, as indicated by NH₃-TPD and DNP-enhanced ¹⁷O{¹H} SSNMR. In situ DRIFTS and XAS hydrogenation experiments reveal the probable formation of a surface Pt(IV)-H upon hydrogenolysis of Pt-Me groups. The heterogenized organoplatinum(IV)-hydride sites catalyze the selective partial hydrogenation of 1,3-butadiene to butenes (up to 95%) and the reduction of nitrobenzene derivatives to anilines (up to 99%) with excellent tolerance of reduction-sensitive functional groups (olefin, carbonyl, nitrile, halogens) under mild reaction conditions.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Ames Laboratory (AMES), Ames, IA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: AC02-06CH11357; AC02-07CH11358

OSTI ID:: 1427735

Report Number(s):: IS-J--9598

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 11 Vol. 140; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (113)

Solvent-Free, Low-Temperature, Selective Hydrogenation of Polyenes using a Bimetallic Nanoparticle Ru-Sn Catalyst Hermans, Sophie; Raja, Robert; Thomas, John M. Angewandte Chemie International Edition, Vol. 40, Issue 7 https://doi.org/10.1002/1521-3773(20010401)40:7<1211::AID-ANIE1211>3.0.CO;2-P	journal	April 2001
Surface Organometallic Chemistry on Oxides: Selective Catalytic Low-Temperature Hydrogenolysis of Alkanes by a Highly Electrophilic Zirconium Hydride Complex Supported on Silica Lecuyer, Christine; Quignard, Francoise; Choplin, Agnès Angewandte Chemie International Edition in English, Vol. 30, Issue 12 https://doi.org/10.1002/anie.199116601	journal	December 1991
Homogeneous and Heterogeneous Catalysis: Bridging the Gap through Surface Organometallic Chemistry Copéret, Christophe; Chabanas, Mathieu; Petroff Saint-Arroman, Romain Angewandte Chemie International Edition, Vol. 42, Issue 2, p. 156-181 https://doi.org/10.1002/anie.200390072	journal	January 2003
A Single-Site Platinum CO Oxidation Catalyst in Zeolite KLTL: Microscopic and Spectroscopic Determination of the Locations of the Platinum Atoms Kistler, Joseph D.; Chotigkrai, Nutchapon; Xu, Pinghong Angewandte Chemie International Edition, Vol. 53, Issue 34 https://doi.org/10.1002/anie.201403353	journal	July 2014
Single-Face/All- cis Arene Hydrogenation by a Supported Single-Site d ⁰ Organozirconium Catalyst Stalzer, Madelyn Marie; Nicholas, Christopher P.; Bhattacharyya, Alak Angewandte Chemie International Edition, Vol. 55, Issue 17 https://doi.org/10.1002/anie.201600345	journal	March 2016
Natural Abundance ¹⁷ O DNP NMR Provides Precise O−H Distances and Insights into the Brønsted Acidity of Heterogeneous Catalysts Perras, Frédéric A.; Wang, Zhuoran; Naik, Pranjali Angewandte Chemie International Edition, Vol. 56, Issue 31 https://doi.org/10.1002/anie.201704032	journal	June 2017
Selective Catalytic Hydrogenation of Functionalized Nitroarenes: An Update Blaser, Hans-Ulrich; Steiner, Heinz; Studer, Martin ChemCatChem, Vol. 1, Issue 2 https://doi.org/10.1002/cctc.200900129	journal	October 2009
195Pt NMR study of (η5-cyclopentadienyl)trialkylplatinum(IV) complexes Boardman, Larry D.; Newmark, Richard A. Magnetic Resonance in Chemistry, Vol. 30, Issue 6 https://doi.org/10.1002/mrc.1260300605	journal	June 1992
Adiabatic Pulses for Wideband Inversion and Broadband Decoupling Kupce, E.; Freeman, R. Journal of Magnetic Resonance, Series A, Vol. 115, Issue 2 https://doi.org/10.1006/jmra.1995.1179	journal	August 1995
QCPMG-MAS NMR of Half-Integer Quadrupolar Nuclei Larsen, Flemming H.; Jakobsen, Hans J.; Ellis, Paul D. Journal of Magnetic Resonance, Vol. 131, Issue 1 https://doi.org/10.1006/jmre.1997.1341	journal	March 1998
Supported Single-Site Organometallic Catalysts for the Synthesis of High-Performance Polyolefins Stalzer, Madelyn M.; Delferro, Massimiliano; Marks, Tobin J. Catalysis Letters, Vol. 145, Issue 1, p. 3-14 https://doi.org/10.1007/s10562-014-1427-x	journal	November 2014
State of the Art and Perspectives in the “Molecular Approach” Towards Well-Defined Heterogeneous Catalysts Conley, Matthew P.; Copéret, Christophe Topics in Catalysis, Vol. 57, Issue 10-13 https://doi.org/10.1007/s11244-014-0245-0	journal	March 2014
Frequency-switched pulse sequences: Homonuclear decoupling and dilute spin NMR in solids Bielecki, A.; Kolbert, A. C.; Levitt, M. H. Chemical Physics Letters, Vol. 155, Issue 4-5 https://doi.org/10.1016/0009-2614(89)87166-0	journal	March 1989
Surface organometallic chemistry on metals Ferretti, O. A.; Bournonville, J. P.; Mabilon, G. Journal of Molecular Catalysis, Vol. 67, Issue 3 https://doi.org/10.1016/0304-5102(91)80040-A	journal	August 1991
The impact of surface organometallic chemistry in heterogeneous catalysis: A new class of highly chemoselective hydrogenation catalysts, RhsSn(n-C4H9)2/SiO2 Didillon, B.; Candy, J. P.; El Mansour, A. Journal of Molecular Catalysis, Vol. 74, Issue 1-3 https://doi.org/10.1016/0304-5102(92)80222-3	journal	July 1992
Surface organometallic chemistry on metals: a novel and effective route to custom-designed bimetallic catalysts Candy, Jean-Pierre; Didillon, Blaise; Smith, Earl L. Journal of Molecular Catalysis, Vol. 86, Issue 1-3 https://doi.org/10.1016/0304-5102(93)E0211-X	journal	January 1994
Surface organometallic chemistry on metals preparation of new selective bimetallic catalysts by reaction of tetra-n-butyl tin with silica supported Rh, Ru and Ni Agnelli, M.; Louessard, P.; El Mansour, A. Catalysis Today, Vol. 6, Issue 1-2 https://doi.org/10.1016/0920-5861(89)85007-2	journal	October 1989
8.16 Heterogeneous Hydrogenation of CC and CC Bonds Thomas, S. P.; Greenhalgh, M. D. Comprehensive Organic Synthesis II https://doi.org/10.1016/B978-0-08-097742-3.00818-1	book	January 2014
Catalytic syntheses of aromatic amines Downing, R. S.; Kunkeler, P. J.; van Bekkum, H. Catalysis Today, Vol. 37, Issue 2 https://doi.org/10.1016/S0920-5861(97)00005-9	journal	August 1997
The role of catalysis for the clean production of fine chemicals Blaser, Hans-Ulrich; Studer, Martin Applied Catalysis A: General, Vol. 189, Issue 2 https://doi.org/10.1016/S0926-860X(99)00276-8	journal	December 1999
Hydrogenation of crotonaldehyde on Pt/SiO2 catalysts modified with tin added via surface organometallic chemistry on metals techniques Santori, Gerardo F.; Casella, Mónica L.; Siri, Guillermo J. Applied Catalysis A: General, Vol. 197, Issue 1 https://doi.org/10.1016/S0926-860X(99)00548-7	journal	April 2000
Hydrogenation of carbonyl compounds using tin-modified platinum-based catalysts prepared via surface organometallic chemistry on metals (SOMC/M) Santori, Gerardo F.; Casella, Mónica L.; Ferretti, Osmar A. Journal of Molecular Catalysis A: Chemical, Vol. 186, Issue 1-2 https://doi.org/10.1016/S1381-1169(02)00188-7	journal	July 2002
Silica-supported alkylidene complexes: their preparation, characterization and reactivity, especially towards olefins Beaudoin, Marcel C.; Womiloju, Omisola; Fu, Anqiu Journal of Molecular Catalysis A: Chemical, Vol. 190, Issue 1-2 https://doi.org/10.1016/S1381-1169(02)00248-0	journal	December 2002
Recent applications in catalysis of surface organometallic chemistry Lefebvre, Frédéric; Basset, Jean-Marie Journal of Molecular Catalysis A: Chemical, Vol. 146, Issue 1-2 https://doi.org/10.1016/S1381-1169(99)00104-1	journal	October 1999
Surface properties and catalytic performance of Pt–Ag supported on silica – The effect of preparation methods Czaplinska, Joanna; Decyk, Piotr; Ziolek, Maria Applied Catalysis A: General, Vol. 504 https://doi.org/10.1016/j.apcata.2014.12.054	journal	September 2015
QCPMG using adiabatic pulses for faster acquisition of ultra-wideline NMR spectra O’Dell, Luke A.; Schurko, Robert W. Chemical Physics Letters, Vol. 464, Issue 1-3 https://doi.org/10.1016/j.cplett.2008.08.095	journal	October 2008
Particle size effects on the reducibility of titanium dioxide and its relation to the water–gas shift activity of Pt/TiO2 catalysts Panagiotopoulou, P.; Christodoulakis, A.; Kondarides, D. I. Journal of Catalysis, Vol. 240, Issue 2 https://doi.org/10.1016/j.jcat.2006.03.012	journal	June 2006
Design of highly active and chemoselective bimetallic gold–platinum hydrogenation catalysts through kinetic and isotopic studies Serna, Pedro; Concepción, Patricia; Corma, Avelino Journal of Catalysis, Vol. 265, Issue 1 https://doi.org/10.1016/j.jcat.2009.04.004	journal	July 2009
Single-site zinc on silica catalysts for propylene hydrogenation and propane dehydrogenation: Synthesis and reactivity evaluation using an integrated atomic layer deposition-catalysis instrument Camacho-Bunquin, Jeffrey; Aich, Payoli; Ferrandon, Magali Journal of Catalysis, Vol. 345 https://doi.org/10.1016/j.jcat.2016.10.017	journal	January 2017
Measurements of motionally averaged heteronuclear dipolar couplings in MAS NMR using R-type recoupling Dvinskikh, Sergey V.; Zimmermann, Herbert; Maliniak, Arnold Journal of Magnetic Resonance, Vol. 168, Issue 2 https://doi.org/10.1016/j.jmr.2004.03.001	journal	June 2004
Broadband adiabatic inversion pulses for cross polarization in wideline solid-state NMR spectroscopy Harris, Kristopher J.; Lupulescu, Adonis; Lucier, Bryan E. G. Journal of Magnetic Resonance, Vol. 224 https://doi.org/10.1016/j.jmr.2012.08.015	journal	November 2012
Windowed R-PDLF recoupling: A flexible and reliable tool to characterize molecular dynamics Gansmüller, Axel; Simorre, Jean-Pierre; Hediger, Sabine Journal of Magnetic Resonance, Vol. 234 https://doi.org/10.1016/j.jmr.2013.06.017	journal	September 2013
Catalytic significance of organometallic compounds immobilized on mesoporous silica: economically and environmentally important examples Thomas, John Meurig; Raja, Robert Journal of Organometallic Chemistry, Vol. 689, Issue 24 https://doi.org/10.1016/j.jorganchem.2004.07.052	journal	November 2004
Improved strategies for DNP-enhanced 2D 1H-X heteronuclear correlation spectroscopy of surfaces Kobayashi, Takeshi; Perras, Frédéric A.; Chaudhary, Umesh Solid State Nuclear Magnetic Resonance, Vol. 87 https://doi.org/10.1016/j.ssnmr.2017.08.002	journal	October 2017
Catalysis by Design: Well-Defined Single-Site Heterogeneous Catalysts Pelletier, Jérémie D. A.; Basset, Jean-Marie Accounts of Chemical Research, Vol. 49, Issue 4 https://doi.org/10.1021/acs.accounts.5b00518	journal	March 2016
Surface Organometallic and Coordination Chemistry toward Single-Site Heterogeneous Catalysts: Strategies, Methods, Structures, and Activities Copéret, Christophe; Comas-Vives, Aleix; Conley, Matthew P. Chemical Reviews, Vol. 116, Issue 2 https://doi.org/10.1021/acs.chemrev.5b00373	journal	January 2016
Isolated Surface Hydrides: Formation, Structure, and Reactivity Copéret, Christophe; Estes, Deven P.; Larmier, Kim Chemical Reviews, Vol. 116, Issue 15 https://doi.org/10.1021/acs.chemrev.6b00082	journal	June 2016
Selective Grafting of Ga( i- Bu) ₃ on the Silanols of Mesoporous H-ZSM-5 by Surface Organometallic Chemistry Szeto, Kai C.; Gallo, Alessandro; Hernández-Morejudo, Selene The Journal of Physical Chemistry C, Vol. 119, Issue 47 https://doi.org/10.1021/acs.jpcc.5b09289	journal	November 2015
DNP-Enhanced Ultrawideline Solid-State NMR Spectroscopy: Studies of Platinum in Metal–Organic Frameworks Kobayashi, Takeshi; Perras, Frédéric A.; Goh, Tian Wei The Journal of Physical Chemistry Letters, Vol. 7, Issue 13 https://doi.org/10.1021/acs.jpclett.6b00860	journal	June 2016
Stabilizing Single-Atom and Small-Domain Platinum via Combining Organometallic Chemisorption and Atomic Layer Deposition Liu, Shengsi; Tan, J. Miles; Gulec, Ahmet Organometallics, Vol. 36, Issue 4 https://doi.org/10.1021/acs.organomet.6b00869	journal	February 2017
Effect of Siloxane Ring Strain and Cation Charge Density on the Formation of Coordinately Unsaturated Metal Sites on Silica: Insights from Density Functional Theory (DFT) Studies Das, Ujjal; Zhang, Guanghui; Hu, Bo ACS Catalysis, Vol. 5, Issue 12 https://doi.org/10.1021/acscatal.5b01699	journal	November 2015
Transforming Nano Metal Nonselective Particulates into Chemoselective Catalysts for Hydrogenation of Substituted Nitrobenzenes Serna, Pedro; Corma, Avelino ACS Catalysis, Vol. 5, Issue 12 https://doi.org/10.1021/acscatal.5b01846	journal	November 2015
Dynamic Nuclear Polarization Solid-State NMR in Heterogeneous Catalysis Research Kobayashi, Takeshi; Perras, Frédéric A.; Slowing, Igor I. ACS Catalysis, Vol. 5, Issue 12 https://doi.org/10.1021/acscatal.5b02039	journal	October 2015
Efficient Catalytic System for Chemoselective Hydrogenation of Halonitrobenzene to Haloaniline Using PtZn Intermetallic Compound Iihama, Sho; Furukawa, Shinya; Komatsu, Takayuki ACS Catalysis, Vol. 6, Issue 2 https://doi.org/10.1021/acscatal.5b02464	journal	December 2015
Catalysis by Supported Single Metal Atoms Liu, Jingyue ACS Catalysis, Vol. 7, Issue 1 https://doi.org/10.1021/acscatal.6b01534	journal	November 2016
Reactivity of a Carbon-Supported Single-Site Molybdenum Dioxo Catalyst for Biodiesel Synthesis Mouat, Aidan R.; Lohr, Tracy L.; Wegener, Evan C. ACS Catalysis, Vol. 6, Issue 10 https://doi.org/10.1021/acscatal.6b01717	journal	September 2016
One-Electron-Redox Activation of the Reduced Phillips Polymerization Catalyst, via Alkylchromium(IV) Homolysis: A Computational Assessment Fong, Anthony; Peters, Baron; Scott, Susannah L. ACS Catalysis, Vol. 6, Issue 9 https://doi.org/10.1021/acscatal.6b01728	journal	August 2016
Direct Synthesis of Low-Coordinate Pd Catalysts Supported on SiO ₂ via Surface Organometallic Chemistry Liu, Shengsi; Tan, J. Miles; Gulec, Ahmet ACS Catalysis, Vol. 6, Issue 12 https://doi.org/10.1021/acscatal.6b02046	journal	November 2016
Supported Aluminum Catalysts for Olefin Hydrogenation Camacho-Bunquin, Jeffrey; Ferrandon, Magali; Das, Ujjal ACS Catalysis, Vol. 7, Issue 1 https://doi.org/10.1021/acscatal.6b02771	journal	December 2016
Zinc Promotion of Platinum for Catalytic Light Alkane Dehydrogenation: Insights into Geometric and Electronic Effects Cybulskis, Viktor J.; Bukowski, Brandon C.; Tseng, Han-Ting ACS Catalysis, Vol. 7, Issue 6 https://doi.org/10.1021/acscatal.6b03603	journal	May 2017
Mechanism of Initiation in the Phillips Ethylene Polymerization Catalyst: Ethylene Activation by Cr(II) and the Structure of the Resulting Active Site Brown, Carole; Lita, Adrian; Tao, Yuchuan ACS Catalysis, Vol. 7, Issue 11 https://doi.org/10.1021/acscatal.7b02677	journal	September 2017
Surface-bound metal hydrocarbyls. Organometallic connections between heterogeneous and homogeneous catalysis Marks, Tobin J. Accounts of Chemical Research, Vol. 25, Issue 2 https://doi.org/10.1021/ar00014a001	journal	February 1992
Design Strategies for the Molecular Level Synthesis of Supported Catalysts Wegener, Staci L.; Marks, Tobin J.; Stair, Peter C. Accounts of Chemical Research, Vol. 45, Issue 2 https://doi.org/10.1021/ar2001342	journal	August 2011
Dynamic Nuclear Polarization Surface Enhanced NMR Spectroscopy Rossini, Aaron J.; Zagdoun, Alexandre; Lelli, Moreno Accounts of Chemical Research, Vol. 46, Issue 9 https://doi.org/10.1021/ar300322x	journal	March 2013
Molecular Metal Catalysts on Supports: Organometallic Chemistry Meets Surface Science Serna, Pedro; Gates, Bruce C. Accounts of Chemical Research, Vol. 47, Issue 8 https://doi.org/10.1021/ar500170k	journal	July 2014
Metathesis of Alkanes and Related Reactions Basset, Jean-Marie; Coperet, Christophe; Soulivong, Daravong Accounts of Chemical Research, Vol. 43, Issue 2, p. 323-334 https://doi.org/10.1021/ar900203a	journal	February 2010
Synthesis of Intermetallic PtZn Nanoparticles by Reaction of Pt Nanoparticles with Zn Vapor and Their Application as Fuel Cell Catalysts Miura, Akira; Wang, Hongsen; Leonard, Brian M. Chemistry of Materials, Vol. 21, Issue 13 https://doi.org/10.1021/cm900048e	journal	July 2009
C−H Bond Activation and Organometallic Intermediates on Isolated Metal Centers on Oxide Surfaces Coperet, Christophe Chemical Reviews, Vol. 110, Issue 2 https://doi.org/10.1021/cr900122p	journal	February 2010
Propylene Hydrogenation and Propane Dehydrogenation by a Single-Site Zn ²⁺ on Silica Catalyst Schweitzer, Neil M.; Hu, Bo; Das, Ujjal ACS Catalysis, Vol. 4, Issue 4 https://doi.org/10.1021/cs401116p	journal	March 2014
Characterization of (methylcyclopentadienyl)trimethylplatinum and low-temperature organometallic chemical vapor deposition of platinum metal Xue, Ziling; Strouse, M. Jane; Shuh, David K. Journal of the American Chemical Society, Vol. 111, Issue 24 https://doi.org/10.1021/ja00206a002	journal	November 1989
Cis dihydride diphosphine complexes of platium(II) and their dehydrogenation to form dimeric platinum(0) complexes. The structure of [Pt(tert-Bu)2P(CH2)3P(tert-Bu)2]2 Yoshida, T.; Yamagata, T.; Tulip, T. H. Journal of the American Chemical Society, Vol. 100, Issue 7 https://doi.org/10.1021/ja00475a016	journal	March 1978
Chemistry of Metal Hydrides. I. Reactions of Some Platinum(II) Hydrides Clark, H. C.; Tsang, W. S. Journal of the American Chemical Society, Vol. 89, Issue 3 https://doi.org/10.1021/ja00979a010	journal	February 1967
Preparation of New Catalysts by the Immobilization of Palladium(II) Species onto Silica: An Investigation of Their Catalytic Activity for the Cyclization of Aminoalkynes Richmond, Matthew K.; Scott, Susannah L.; Alper, Howard Journal of the American Chemical Society, Vol. 123, Issue 43 https://doi.org/10.1021/ja0113450	journal	October 2001
Spectroscopically Distinct Sites Present in Methyltrioxorhenium Grafted onto Silica−Alumina, and Their Abilities to Initiate Olefin Metathesis Moses, Anthony W.; Raab, Christina; Nelson, Ryan C. Journal of the American Chemical Society, Vol. 129, Issue 28 https://doi.org/10.1021/ja072707s	journal	July 2007
Surface Enhanced NMR Spectroscopy by Dynamic Nuclear Polarization Lesage, Anne; Lelli, Moreno; Gajan, David Journal of the American Chemical Society, Vol. 132, Issue 44 https://doi.org/10.1021/ja104771z	journal	November 2010
Evidence for the Pairwise Disposition of Grafting Sites on Highly Dehydroxylated Silicas via Their Reactions with Ga(CH ₃ ) ₃ Fleischman, Samuel D.; Scott, Susannah L. Journal of the American Chemical Society, Vol. 133, Issue 13 https://doi.org/10.1021/ja108905p	journal	April 2011
CO Oxidation on Supported Single Pt Atoms: Experimental and ab Initio Density Functional Studies of CO Interaction with Pt Atom on θ-Al ₂ O ₃ (010) Surface Moses-DeBusk, Melanie; Yoon, Mina; Allard, Lawrence F. Journal of the American Chemical Society, Vol. 135, Issue 34 https://doi.org/10.1021/ja401847c	journal	August 2013
Large Molecular Weight Nitroxide Biradicals Providing Efficient Dynamic Nuclear Polarization at Temperatures up to 200 K Zagdoun, Alexandre; Casano, Gilles; Ouari, Olivier Journal of the American Chemical Society, Vol. 135, Issue 34 https://doi.org/10.1021/ja405813t	journal	August 2013
Transforming Nonselective into Chemoselective Metal Catalysts for the Hydrogenation of Substituted Nitroaromatics Corma, Avelino; Serna, Pedro; Concepción, Patricia Journal of the American Chemical Society, Vol. 130, Issue 27 https://doi.org/10.1021/ja800959g	journal	July 2008
Synthesis and Characterization of Silica-Stabilized Chromium(IV) Alkylidene Complexes Amor Nait Ajjou, Jamila; Scott, Susannah L.; Paquet, Valérie Journal of the American Chemical Society, Vol. 120, Issue 2 https://doi.org/10.1021/ja973177a	journal	January 1998
Mono- and Dinuclear Silica-Supported Titanium(IV) Complexes and the Effect of TiOTi Connectivity on Reactivity Bouh, Abdillahi Omar; Rice, Gordon L.; Scott, Susannah L. Journal of the American Chemical Society, Vol. 121, Issue 31 https://doi.org/10.1021/ja9829160	journal	August 1999
Benzene Selectivity in Competitive Arene Hydrogenation: Effects of Single-Site Catalyst···Acidic Oxide Surface Binding Geometry Gu, Weixing; Stalzer, Madelyn Marie; Nicholas, Christopher P. Journal of the American Chemical Society, Vol. 137, Issue 21, p. 6770-6780 https://doi.org/10.1021/jacs.5b03254	journal	April 2015
Rate-Enhancing Roles of Water Molecules in Methyltrioxorhenium-Catalyzed Olefin Epoxidation by Hydrogen Peroxide Goldsmith, Bryan R.; Hwang, Taeho; Seritan, Stefan Journal of the American Chemical Society, Vol. 137, Issue 30 https://doi.org/10.1021/jacs.5b03750	journal	July 2015
Natural Abundance ¹⁷ O DNP Two-Dimensional and Surface-Enhanced NMR Spectroscopy Perras, Frédéric A.; Kobayashi, Takeshi; Pruski, Marek Journal of the American Chemical Society, Vol. 137, Issue 26 https://doi.org/10.1021/jacs.5b03905	journal	June 2015
Ligand Exchange-Mediated Activation and Stabilization of a Re-Based Olefin Metathesis Catalyst by Chlorinated Alumina Gallo, Alessandro; Fong, Anthony; Szeto, Kai C. Journal of the American Chemical Society, Vol. 138, Issue 39 https://doi.org/10.1021/jacs.6b06953	journal	September 2016
Silica-Supported Cu Nanoparticle Catalysts for Alkyne Semihydrogenation: Effect of Ligands on Rates and Selectivity Fedorov, Alexey; Liu, Hsueh-Ju; Lo, Hung-Kun Journal of the American Chemical Society, Vol. 138, Issue 50 https://doi.org/10.1021/jacs.6b10817	journal	December 2016
Sub-4 nm PtZn Intermetallic Nanoparticles for Enhanced Mass and Specific Activities in Catalytic Electrooxidation Reaction Qi, Zhiyuan; Xiao, Chaoxian; Liu, Cong Journal of the American Chemical Society, Vol. 139, Issue 13 https://doi.org/10.1021/jacs.6b12780	journal	March 2017
Mode of Adsorption of (CH ₃ ) ₂ Au(acac) onto Partially Dehydroxylated Silica Hisamoto, Miyako; Nelson, Ryan C.; Lee, Ming-Yung The Journal of Physical Chemistry C, Vol. 113, Issue 20 https://doi.org/10.1021/jp810057v	journal	May 2009
Stability of PtZn Nanoparticles Supported on Carbon in Acidic Electrochemical Environments Sode, Aya; Musgrove, Amanda; Bizzotto, Dan The Journal of Physical Chemistry C, Vol. 114, Issue 1 https://doi.org/10.1021/jp909103w	journal	December 2009
Mobility of Surface Species on Oxides. 2. Isotopic Exchange of D ₂ with H of SiO ₂ , Al ₂ O ₃ , ZrO ₂ , MgO, and CeO ₂ : Activation by Rhodium and Effect of Chlorine Martin, Dominique; Duprez, Daniel The Journal of Physical Chemistry B, Vol. 101, Issue 22 https://doi.org/10.1021/jp970050z	journal	May 1997
Preparation of Dinuclear Phosphine-Bridged Palladium(II) Species and Their Silica-Bound Analogues as Catalysts for the Cyclization of Aminoalkynes Richmond, Matthew K.; Scott, Susannah L.; Yap, Glenn P. A. Organometallics, Vol. 21, Issue 16 https://doi.org/10.1021/om020026u	journal	August 2002
Methyltrioxorhenium Interactions with Lewis Acid Sites of an Amorphous Silica−Alumina Moses, Anthony W.; Ramsahye, Naseem A.; Raab, Christina Organometallics, Vol. 25, Issue 9 https://doi.org/10.1021/om050962k	journal	March 2006
Reactions of Tetraalkylchromium(IV) with Silica: Mechanism of Grafting and Characterization of Surface Organometallic Complexes Amor Nait Ajjou, Jamila; Scott, Susannah L. Organometallics, Vol. 16, Issue 1 https://doi.org/10.1021/om960612l	journal	January 1997
Synthesis and Structural Characterization of an Authentic Platinum(IV) Carbonyl Compound Forniés, Juan; Gómez-Saso, Miguel A.; Martín, Antonio Organometallics, Vol. 16, Issue 26 https://doi.org/10.1021/om970651c	journal	December 1997
Stable Cationic Dimethyl(hydrido)platinum(IV) Complex Prokopchuk, Ernest M.; Jenkins, Hilary A.; Puddephatt, Richard J. Organometallics, Vol. 18, Issue 15 https://doi.org/10.1021/om990205k	journal	July 1999
Selective hydrogenation of ά,β-unsaturated aldehydes and other C=O and C=C bonds containing compounds Claus, Peter Topics In Catalysis, Vol. 5, Issue 1/4, p. 51-62 https://doi.org/10.1023/A:1019177330810	journal	January 1998
Single-atom catalysis of CO oxidation using Pt1/FeOx Qiao, Botao; Wang, Aiqin; Yang, Xiaofeng Nature Chemistry, Vol. 3, Issue 8 https://doi.org/10.1038/nchem.1095	journal	July 2011
FeOx-supported platinum single-atom and pseudo-single-atom catalysts for chemoselective hydrogenation of functionalized nitroarenes Wei, Haisheng; Liu, Xiaoyan; Wang, Aiqin Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms6634	journal	December 2014
Near-field dielectric scattering promotes optical absorption by platinum nanoparticles Zhang, Nan; Han, Chuang; Xu, Yi-Jun Nature Photonics, Vol. 10, Issue 7 https://doi.org/10.1038/nphoton.2016.76	journal	May 2016
195Pt NMR—theory and application Still, Brett M.; Kumar, P. G. Anil; Aldrich-Wright, Janice R. Chem. Soc. Rev., Vol. 36, Issue 4 https://doi.org/10.1039/B606190G	journal	January 2007
Highly efficient and selective photocatalytic hydrogenation of functionalized nitrobenzenes Yang, Xiu-Jie; Chen, Bin; Zheng, Li-Qiang Green Chem., Vol. 16, Issue 3 https://doi.org/10.1039/C3GC42042F	journal	January 2014
A recoverable Pd nanocatalyst for selective semi-hydrogenation of alkynes: hydrogenation of benzyl-propargylamines as a challenging model Uberman, Paula M.; Costa, Natalia J. S.; Philippot, Karine Green Chem., Vol. 16, Issue 10 https://doi.org/10.1039/C4GC00669K	journal	January 2014
Structurally ordered Pt–Zn/C series nanoparticles as efficient anode catalysts for formic acid electrooxidation Zhu, Jing; Zheng, Xin; Wang, Jie Journal of Materials Chemistry A, Vol. 3, Issue 44 https://doi.org/10.1039/C5TA05699C	journal	January 2015
Efficient catalytic greenhouse gas-free hydrogen and aldehyde formation from aqueous alcohol solutions Lohr, Tracy L.; Mouat, Aidan R.; Schweitzer, Neil M. Energy & Environmental Science, Vol. 10, Issue 7 https://doi.org/10.1039/C6EE03739A	journal	January 2017
Silica supported copper nanoparticles prepared via surface organometallic chemistry: active catalysts for the selective hydrogenation of 2,3-dimethylbutadiene Boukebbous, K.; Merle, N.; Larabi, C. New Journal of Chemistry, Vol. 41, Issue 2 https://doi.org/10.1039/C6NJ03350D	journal	January 2017
Isolated, well-defined organovanadium( iii ) on silica: single-site catalyst for hydrogenation of alkenes and alkynes Sohn, H.; Camacho-Bunquin, J.; Langeslay, R. R. Chemical Communications, Vol. 53, Issue 53 https://doi.org/10.1039/C7CC01876B	journal	January 2017
Synergistic effects in Fe nanoparticles doped with ppm levels of (Pd + Ni). A new catalyst for sustainable nitro group reductions Pang, Haobo; Gallou, Fabrice; Sohn, Hyuntae Green Chemistry, Vol. 20, Issue 1 https://doi.org/10.1039/C7GC02991H	journal	January 2018
Monitoring photoswitching of azobenzene-based self-assembled monolayers on ultrathin platinum films by UV/Vis spectroscopy in the transmission modeElectronic supplementary information (ESI) available: synthesis and characterization of 1 and its photoisomerization in solution. See http://www.rsc.org/suppdata/jm/b3/b314710j/ Sortino, Salvatore; Petralia, Salvatore; Conoci, Sabrina Journal of Materials Chemistry, Vol. 14, Issue 5 https://doi.org/10.1039/b314710j	journal	January 2004
Platinum species in the pores of NaX, NaY and NaA zeolites studied using EPR, XAS and FTIR spectroscopies Akdogan, Yasar; Vogt, Christina; Bauer, Matthias Physical Chemistry Chemical Physics, Vol. 10, Issue 20 https://doi.org/10.1039/b718932j	journal	January 2008
Chemoselective reduction of nitrobenzenes to aminobenzenes having reducible groups by a titanium(iv) oxide photocatalyst under gas- and metal-free conditions Imamura, Kazuya; Hashimoto, Keiji; Kominami, Hiroshi Chemical Communications, Vol. 48, Issue 36 https://doi.org/10.1039/c2cc31524f	journal	January 2012
Infrared spectra and density functional calculations of platinum hydrides Andrews, Lester; Wang, Xeufeng; Manceron, Laurent The Journal of Chemical Physics, Vol. 114, Issue 4 https://doi.org/10.1063/1.1333020	journal	January 2001
Dynamic nuclear polarization at high magnetic fields Maly, Thorsten; Debelouchina, Galia T.; Bajaj, Vikram S. The Journal of Chemical Physics, Vol. 128, Issue 5 https://doi.org/10.1063/1.2833582	journal	February 2008
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr Schäfer, Ansgar; Huber, Christian; Ahlrichs, Reinhart The Journal of Chemical Physics, Vol. 100, Issue 8 https://doi.org/10.1063/1.467146	journal	April 1994
Catalyst synthesis and evaluation using an integrated atomic layer deposition synthesis–catalysis testing tool Camacho-Bunquin, Jeffrey; Shou, Heng; Aich, Payoli Review of Scientific Instruments, Vol. 86, Issue 8 https://doi.org/10.1063/1.4928614	journal	August 2015
Surface structural-chemical characterization of a single-site d0 heterogeneous arene hydrogenation catalyst having 100% active sites Williams, L. A.; Guo, N.; Motta, A. Proceedings of the National Academy of Sciences, Vol. 110, Issue 2 https://doi.org/10.1073/pnas.1220240110	journal	December 2012
The Contribution of Organometallic Chemistry and Homogeneous Catalysis to the Understanding of Surface Reactions Ugo, R. Catalysis Reviews, Vol. 11, Issue 1 https://doi.org/10.1080/01614947508079986	journal	January 1975
Selective Hydrogenation of α,β-Unsaturated Aldehydes Gallezot, P.; Richard, D. Catalysis Reviews, Vol. 40, Issue 1-2 https://doi.org/10.1080/01614949808007106	journal	February 1998
Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Lee, Chengteh; Yang, Weitao; Parr, Robert G. Physical Review B, Vol. 37, Issue 2 https://doi.org/10.1103/PhysRevB.37.785	journal	January 1988
Chemoselective Hydrogenation of Nitro Compounds with Supported Gold Catalysts Corma, Avelino; Serna, Pedro Science, Vol. 313, Issue 5785, p. 332-334 https://doi.org/10.1126/science.1128383	journal	July 2006
Identification of active sites in CO oxidation and water-gas shift over supported Pt catalysts Ding, K.; Gulec, A.; Johnson, A. M. Science, Vol. 350, Issue 6257 https://doi.org/10.1126/science.aac6368	journal	September 2015
Recent Development of Palladium-Supported Catalysts for Chemoselective Hydrogenation Monguchi, Yasunari; Ichikawa, Tomohiro; Sajiki, Hironao CHEMICAL & PHARMACEUTICAL BULLETIN, Vol. 65, Issue 1 https://doi.org/10.1248/cpb.c16-00153	journal	January 2017
Silica-supported PtSn Catalysts Obtained Through Surface Organometallic Chemistry on Metals Techniques Using a Hydrosoluble Organotin Promoter. Application to the Selective Hydrogenation of α, β-Unsaturated Aldehydes and Ketones Merlo, Andrea; Vetere, Virginia; Casell, Monica Current Catalysis, Vol. 3, Issue 2 https://doi.org/10.2174/2211544702666140107000909	journal	August 2014

Cited By (6)

Fe/Fe ₂ O ₃ @N-dopped Porous Carbon: A High-Performance Catalyst for Selective Hydrogenation of Nitro Compounds Yun, Ruirui; Hong, Lirui; Ma, Wanjiao ChemCatChem, Vol. 11, Issue 2 https://doi.org/10.1002/cctc.201801626	journal	December 2018
Structural Insights into Peptides Bound to the Surface of Silica Nanopores Brodrecht, Martin; Kumari, Bharti; Thankamony, A. S. Sofia Lilly Chemistry – A European Journal, Vol. 25, Issue 20 https://doi.org/10.1002/chem.201805480	journal	March 2019
A Review on the Recent Advances in the Reductions of Carbon–Carbon/Oxygen Multiple Bonds Including Aromatic Rings Using Raney Ni–Al Alloy or Al Powder in the Presence of Noble Metal Catalysts in Water Rayhan, Ummey; Kowser, Zannatul; Islam, Md. Nurul Topics in Catalysis, Vol. 61, Issue 7-8 https://doi.org/10.1007/s11244-018-0994-2	journal	May 2018
Shedding light on the atomic-scale structure of amorphous silica–alumina and its Brønsted acid sites Perras, Frédéric A.; Wang, Zichun; Kobayashi, Takeshi Physical Chemistry Chemical Physics, Vol. 21, Issue 35 https://doi.org/10.1039/c9cp04099d	journal	January 2019
Understanding chemical and physical mechanisms in atomic layer deposition Richey, Nathaniel E.; de Paula, Camila; Bent, Stacey F. The Journal of Chemical Physics, Vol. 152, Issue 4 https://doi.org/10.1063/1.5133390	journal	January 2020
Shedding light on the atomic-scale structure of amorphous silica-alumina and its Brønsted acid sites Perras, Frédéric A.; Wang, Zichun; Kobayashi, Takeshi ETH Zurich https://doi.org/10.3929/ethz-b-000364135	text	January 2019

Similar Records

Characterization of (methylcyclopentadienyl)trimethylplatinum and low-temperature organometallic chemical vapor deposition of platinum metal

Journal Article · Wed Nov 22 04:00:00 UTC 1989 · Journal of the American Chemical Society; (USA) · OSTI ID:7197763

Xue, Ziling; Strouse, M J; Shuh, D K; +4 more

Activation of aromatic carbon-fluorine bonds by organoplatinum complexes

Journal Article · Sun Mar 01 04:00:00 UTC 1992 · Organometallics · OSTI ID:415028

Anderson, C M; Puddephatt, R J; Crespo, M

Electrophilic Organoiridium(III) Pincer Complexes on Sulfated Zirconia for Hydrocarbon Activation and Functionalization

Journal Article · Mon Apr 22 04:00:00 UTC 2019 · Journal of the American Chemical Society · OSTI ID:1509486

Syed, Zoha H.; Kaphan, David M.; Perras, Frédéric A.; +9 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Title: Chemoselective Hydrogenation with Supported Organoplatinum(IV) Catalyst on Zn(II)-Modified Silica

Citation Formats

References (113)

Cited By (6)

Similar Records

Related Subjects