Selective Oxygen-Assisted Reactions of Alcohols and Amines Catalyzed by Metallic Gold: Paradigms for the Design of Catalytic Processes
Abstract
Metallic gold has emerged as a highly successful catalyst for selective oxygen-assisted coupling reactions of alcohols and amines to yield industrially important classes of molecules, including esters and amides. In expanding the substrate scope of this class of reactions, fundamental mechanistic principles determined for simple model systems have been used to predict new reactive pathways for other more complex molecular transformations. Given the importance of these fundamental reaction paradigms, this review aims to consolidate the understanding of oxygen-assisted coupling mechanisms on metallic gold catalysts across a broad range of reported studies, including gas-phase and liquid-phase systems. Furthermore, the review indicates areas where additional understanding is still needed, and where collaboration between the gas-phase and liquid-phase catalysis communities would be instrumental in the elucidation of detailed reaction mechanisms.
- Authors:
-
- Wesleyan Univ., Middletown, CT (United States)
- Harvard Univ., Cambridge, MA (United States)
- Publication Date:
- Research Org.:
- Energy Frontier Research Centers (EFRC) (United States). Integrated Mesoscale Architectures for Sustainable Catalysis (IMASC)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1388703
- Grant/Contract Number:
- SC0012573
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ACS Catalysis
- Additional Journal Information:
- Journal Volume: 7; Journal Issue: 2; Related Information: IMASC partners with Harvard University (lead); Fritz Haber Institute; Lawrence Berkeley National Laboratory; Lawrence Livermore National Laboratory; University of Kansas; Tufts University; Journal ID: ISSN 2155-5435
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; catalysis (heterogeneous); mesostructured materials; materials and chemistry by design; synthesis (novel materials)
Citation Formats
Personick, Michelle L., Madix, Robert J., and Friend, Cynthia M. Selective Oxygen-Assisted Reactions of Alcohols and Amines Catalyzed by Metallic Gold: Paradigms for the Design of Catalytic Processes. United States: N. p., 2016.
Web. doi:10.1021/acscatal.6b02693.
Personick, Michelle L., Madix, Robert J., & Friend, Cynthia M. Selective Oxygen-Assisted Reactions of Alcohols and Amines Catalyzed by Metallic Gold: Paradigms for the Design of Catalytic Processes. United States. https://doi.org/10.1021/acscatal.6b02693
Personick, Michelle L., Madix, Robert J., and Friend, Cynthia M. Fri .
"Selective Oxygen-Assisted Reactions of Alcohols and Amines Catalyzed by Metallic Gold: Paradigms for the Design of Catalytic Processes". United States. https://doi.org/10.1021/acscatal.6b02693. https://www.osti.gov/servlets/purl/1388703.
@article{osti_1388703,
title = {Selective Oxygen-Assisted Reactions of Alcohols and Amines Catalyzed by Metallic Gold: Paradigms for the Design of Catalytic Processes},
author = {Personick, Michelle L. and Madix, Robert J. and Friend, Cynthia M.},
abstractNote = {Metallic gold has emerged as a highly successful catalyst for selective oxygen-assisted coupling reactions of alcohols and amines to yield industrially important classes of molecules, including esters and amides. In expanding the substrate scope of this class of reactions, fundamental mechanistic principles determined for simple model systems have been used to predict new reactive pathways for other more complex molecular transformations. Given the importance of these fundamental reaction paradigms, this review aims to consolidate the understanding of oxygen-assisted coupling mechanisms on metallic gold catalysts across a broad range of reported studies, including gas-phase and liquid-phase systems. Furthermore, the review indicates areas where additional understanding is still needed, and where collaboration between the gas-phase and liquid-phase catalysis communities would be instrumental in the elucidation of detailed reaction mechanisms.},
doi = {10.1021/acscatal.6b02693},
journal = {ACS Catalysis},
number = 2,
volume = 7,
place = {United States},
year = {Fri Dec 30 00:00:00 EST 2016},
month = {Fri Dec 30 00:00:00 EST 2016}
}
Web of Science
Works referenced in this record:
The Medicinal Chemist’s Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates
journal, May 2011
- Roughley, Stephen D.; Jordan, Allan M.
- Journal of Medicinal Chemistry, Vol. 54, Issue 10
Rethinking amide bond synthesis
journal, December 2011
- Pattabiraman, Vijaya R.; Bode, Jeffrey W.
- Nature, Vol. 480, Issue 7378
Aerobic oxidation of aqueous ethanol using heterogeneous gold catalysts: Efficient routes to acetic acid and ethyl acetate
journal, October 2007
- Jorgensen, B.; Egholmchristiansen, S.; Dahlthomsen, M.
- Journal of Catalysis, Vol. 251, Issue 2
Ozone-Activated Nanoporous Gold: A Stable and Storable Material for Catalytic Oxidation
journal, June 2015
- Personick, Michelle L.; Zugic, Branko; Biener, Monika M.
- ACS Catalysis, Vol. 5, Issue 7
Direct visualization of quasi-ordered oxygen chain structures on Au(110)-(1 × 2)
journal, August 2016
- Hiebel, F.; Montemore, M. M.; Kaxiras, E.
- Surface Science, Vol. 650
The oxidation of carbon monoxide on the Au(110) surface
journal, January 1987
- Outka, Duane A.; Madix, R. J.
- Surface Science, Vol. 179, Issue 2-3
Acid-base and nucleophilic chemistry of atomic oxygen on the Au(110) surface: Reactions with formic acid and formaldehyde
journal, January 1987
- Outka, Duane A.; Madix, R. J.
- Surface Science, Vol. 179, Issue 2-3
Broensted basicity of atomic oxygen on the gold(110) surface: reactions with methanol, acetylene, water, and ethylene
journal, March 1987
- Outka, Duane A.; Madix, Robert J.
- Journal of the American Chemical Society, Vol. 109, Issue 6
Novel Gold Catalysts for the Oxidation of Carbon Monoxide at a Temperature far Below 0 °C
journal, February 1987
- Haruta, Masatake; Kobayashi, Tetsuhiko; Sano, Hiroshi
- Chemistry Letters, Vol. 16, Issue 2
Low-Temperature Oxidation of CO over Gold Supported on TiO2, α-Fe2O3, and Co3O4
journal, November 1993
- Haruta, M.; Tsubota, S.; Kobayashi, T.
- Journal of Catalysis, Vol. 144, Issue 1
Selective Vapor-Phase Epoxidation of Propylene over Au/TiO2Catalysts in the Presence of Oxygen and Hydrogen
journal, September 1998
- Hayashi, Toshio; Tanaka, Koji; Haruta, Masatake
- Journal of Catalysis, Vol. 178, Issue 2
Adsorption of oxygen on Au(111) by exposure to ozone
journal, August 1998
- Saliba, N.; Parker, D. H.; Koel, B. E.
- Surface Science, Vol. 410, Issue 2-3
The adsorption of oxygen on gold
journal, June 1984
- Canning, N. D. S.; Outka, D.; Madix, R. J.
- Surface Science, Vol. 141, Issue 1
Oxidation of gold by oxygen-ion sputtering
journal, January 2003
- Gottfried, J. M.; Elghobashi, N.; Schroeder, S. L. M.
- Surface Science, Vol. 523, Issue 1-2
Evidence for Molecularly Chemisorbed Oxygen on TiO 2 Supported Gold Nanoclusters and Au(111)
journal, February 2004
- Stiehl, James D.; Kim, Tae S.; McClure, Sean M.
- Journal of the American Chemical Society, Vol. 126, Issue 6
Chemisorbed Oxygen on Au(111) Produced by a Novel Route: Reaction in Condensed Films of NO 2 + H 2 O
journal, May 1998
- Wang, Jiang; Voss, Michael R.; Busse, Harald
- The Journal of Physical Chemistry B, Vol. 102, Issue 24
Enhancement of O 2 Dissociation on Au(111) by Adsorbed Oxygen: Implications for Oxidation Catalysis
journal, June 2005
- Deng, Xingyi; Min, Byoung Koun; Guloy, Amado
- Journal of the American Chemical Society, Vol. 127, Issue 25
Oxygen-induced restructuring with release of gold atoms from Au(111)
journal, September 2005
- Min, B. K.; Deng, X.; Pinnaduwage, D.
- Physical Review B, Vol. 72, Issue 12
Unraveling molecular transformations on surfaces: a critical comparison of oxidation reactions on coinage metals
journal, January 2008
- Liu, Xiaoying; Madix, Robert J.; Friend, Cynthia M.
- Chemical Society Reviews, Vol. 37, Issue 10
Selectivity Control in Gold-Mediated Esterification of Methanol
journal, May 2009
- Xu, Bingjun; Liu, Xiaoying; Haubrich, Jan
- Angewandte Chemie International Edition, Vol. 48, Issue 23, p. 4206-4209
Reaction of Au(111) with Sulfur and Oxygen: Scanning Tunneling Microscopic Study
journal, August 2005
- Min, B. K.; Alemozafar, A. R.; Biener, M. M.
- Topics in Catalysis, Vol. 36, Issue 1-4
A spectroscopic study of the adsorption and reactions of methanol, formaldehyde and methyl formate on clean and oxygenated Cu(110) surfaces
journal, June 1985
- Sexton, B. A.; Hughes, A. E.; Avery, N. R.
- Surface Science, Vol. 155, Issue 1
Flash desorption activation energies: DCOOH decomposition and CO desorption from Ni (110)
journal, March 1975
- Falconer, J. L.; Madix, R. J.
- Surface Science, Vol. 48, Issue 2
The selective oxidation of CH3OH to H2CO on a copper(110) catalyst
journal, June 1978
- Wachs, I.
- Journal of Catalysis, Vol. 53, Issue 2
Vapour-phase gold-surface-mediated coupling of aldehydes with methanol
journal, November 2009
- Xu, Bingjun; Liu, Xiaoying; Haubrich, Jan
- Nature Chemistry, Vol. 2, Issue 1
Theoretical Study of O-Assisted Selective Coupling of Methanol on Au(111)
journal, February 2011
- Xu, Bingjun; Haubrich, Jan; Baker, Thomas A.
- The Journal of Physical Chemistry C, Vol. 115, Issue 9
Kinetic Prefactors of Reactions on Solid Surfaces
journal, January 2013
- Campbell, Charles T.; Árnadóttir, Líney; Sellers, Jason R. V.
- Zeitschrift für Physikalische Chemie, Vol. 227, Issue 9-11
Primary and secondary kinetic isotope effects for methoxy dehydrogenation and Cu(110): Absence of tunnelling corrections
journal, May 1995
- Madix, R. J.; Telford, S. G.
- Surface Science, Vol. 328, Issue 3
Mechanistic Investigation of the Gold-catalyzed Aerobic Oxidation of Alcohols
journal, October 2007
- Fristrup, Peter; Johansen, Louise Bahn; Christensen, Claus Hviid
- Catalysis Letters, Vol. 120, Issue 3-4
The selective oxidation of ethylene glycol and 1,2-propanediol on Au, Pd, and Au–Pd bimetallic catalysts
journal, November 2013
- Griffin, Michael B.; Rodriguez, Abraham A.; Montemore, Matthew M.
- Journal of Catalysis, Vol. 307
Reactivity of the Gold/Water Interface During Selective Oxidation Catalysis
journal, September 2010
- Zope, B. N.; Hibbitts, D. D.; Neurock, M.
- Science, Vol. 330, Issue 6000
Transient hydroxyl formation from water on oxygen-covered Au(111)
journal, August 2008
- Quiller, R. G.; Baker, T. A.; Deng, X.
- The Journal of Chemical Physics, Vol. 129, Issue 6
A Water-Promoted Mechanism of Alcohol Oxidation on a Au(111) Surface: Understanding the Catalytic Behavior of Bulk Gold
journal, July 2013
- Chang, Chun-Ran; Yang, Xiao-Feng; Long, Bo
- ACS Catalysis, Vol. 3, Issue 8
Origin and Activity of Gold Nanoparticles as Aerobic Oxidation Catalysts in Aqueous Solution
journal, June 2011
- Shang, Cheng; Liu, Zhi-Pan
- Journal of the American Chemical Society, Vol. 133, Issue 25
CO Oxidation on Rutile-Supported Au Nanoparticles
journal, February 2005
- Remediakis, Ioannis N.; Lopez, Nuria; Nørskov, Jens K.
- Angewandte Chemie International Edition, Vol. 44, Issue 12
Catalytic CO Oxidation by a Gold Nanoparticle: A Density Functional Study
journal, September 2002
- Lopez, Nuria; Nørskov, Jens K.
- Journal of the American Chemical Society, Vol. 124, Issue 38
Trends in CO Oxidation Rates for Metal Nanoparticles and Close-Packed, Stepped, and Kinked Surfaces
journal, May 2009
- Jiang, T.; Mowbray, D. J.; Dobrin, S.
- The Journal of Physical Chemistry C, Vol. 113, Issue 24
Towards the computational design of solid catalysts
journal, April 2009
- Nørskov, J.; Bligaard, T.; Rossmeisl, J.
- Nature Chemistry, Vol. 1, Issue 1, p. 37-46
Scaling Relationships for Adsorption Energies on Transition Metal Oxide, Sulfide, and Nitride Surfaces
journal, June 2008
- Fernández, Eva M.; Moses, Poul G.; Toftelund, Anja
- Angewandte Chemie International Edition, Vol. 47, Issue 25
A paradigm for predicting selective oxidation on noble metals: oxidative catalytic coupling of amines and aldehydes on metallic gold
journal, January 2011
- Xu, Bingjun; Friend, Cynthia M.; Madix, Robert J.
- Faraday Discussions, Vol. 152
Role of Surface-Bound Intermediates in the Oxygen-Assisted Synthesis of Amides by Metallic Silver and Gold
journal, July 2012
- Siler, Cassandra G. F.; Xu, Bingjun; Madix, Robert J.
- Journal of the American Chemical Society, Vol. 134, Issue 30
Dual-Function of Alcohols in Gold-Mediated Selective Coupling of Amines and Alcohols
journal, January 2012
- Xu, Bingjun; Madix, Robert J.; Friend, Cynthia M.
- Chemistry - A European Journal, Vol. 18, Issue 8
Activated Metallic Gold as an Agent for Direct Methoxycarbonylation
journal, December 2011
- Xu, Bingjun; Madix, Robert J.; Friend, Cynthia M.
- Journal of the American Chemical Society, Vol. 133, Issue 50
Nanoporous Gold Catalysts for Selective Gas-Phase Oxidative Coupling of Methanol at Low Temperature
journal, January 2010
- Wittstock, A.; Zielasek, V.; Biener, J.
- Science, Vol. 327, Issue 5963
Active site densities, oxygen activation and adsorbed reactive oxygen in alcohol activation on npAu catalysts
journal, January 2016
- Wang, Lu-Cun; Friend, C. M.; Fushimi, Rebecca
- Faraday Discussions, Vol. 188
Catalyst Parameters Determining Activity and Selectivity of Supported Gold Nanoparticles for the Aerobic Oxidation of Alcohols: The Molecular Reaction Mechanism
journal, November 2007
- Abad, Alberto; Corma, Avelino; García, Hermenegildo
- Chemistry - A European Journal, Vol. 14, Issue 1
Efficient chemoselective alcohol oxidation using oxygen as oxidant. Superior performance of gold over palladium catalysts
journal, July 2006
- Abad, Alberto; Almela, Carles; Corma, Avelino
- Tetrahedron, Vol. 62, Issue 28
Evolution of nanoporosity in dealloying
journal, March 2001
- Erlebacher, Jonah; Aziz, Michael J.; Karma, Alain
- Nature, Vol. 410, Issue 6827, p. 450-453
Low Temperature CO Oxidation over Unsupported Nanoporous Gold
journal, January 2007
- Xu, Caixia; Su, Jixin; Xu, Xiaohong
- Journal of the American Chemical Society, Vol. 129, Issue 1, p. 42-43
Nanoporous Gold: Understanding the Origin of the Reactivity of a 21st Century Catalyst Made by Pre-Columbian Technology
journal, September 2015
- Biener, Juergen; Biener, Monika M.; Madix, Robert J.
- ACS Catalysis, Vol. 5, Issue 11
On the Microstructure of Nanoporous Gold: An X-ray Diffraction Study
journal, March 2009
- Petegem, Steven Van; Brandstetter, Stefan; Maass, Robert
- Nano Letters, Vol. 9, Issue 3, p. 1158-1163
Atomic origins of the high catalytic activity of nanoporous gold
journal, August 2012
- Fujita, Takeshi; Guan, Pengfei; McKenna, Keith
- Nature Materials, Vol. 11, Issue 9
Facile Ester Synthesis on Ag-Modified Nanoporous Au: Oxidative Coupling of Ethanol and 1-Butanol Under UHV Conditions
journal, April 2015
- Stowers, Kara J.; Madix, Robert J.; Biener, Monika M.
- Catalysis Letters, Vol. 145, Issue 6
From model studies on Au(111) to working conditions with unsupported nanoporous gold catalysts: Oxygen-assisted coupling reactions
journal, December 2013
- Stowers, K. J.; Madix, R. J.; Friend, C. M.
- Journal of Catalysis, Vol. 308
Catalytic production of methyl acrylates by gold-mediated cross coupling of unsaturated aldehydes with methanol
journal, October 2016
- Karakalos, Stavros; Zugic, Branko; Stowers, Kara J.
- Surface Science, Vol. 652
Continuous Catalytic Production of Methyl Acrylates from Unsaturated Alcohols by Gold: The Strong Effect of C═C Unsaturation on Reaction Selectivity
journal, February 2016
- Zugic, Branko; Karakalos, Stavros; Stowers, Kara J.
- ACS Catalysis, Vol. 6, Issue 3
Active sites for methanol partial oxidation on nanoporous gold catalysts
journal, December 2016
- Wang, Lu-Cun; Personick, Michelle L.; Karakalos, Stavros
- Journal of Catalysis, Vol. 344
Atomic Observation of Catalysis-Induced Nanopore Coarsening of Nanoporous Gold
journal, February 2014
- Fujita, Takeshi; Tokunaga, Tomoharu; Zhang, Ling
- Nano Letters, Vol. 14, Issue 3
Achieving Optimum Selectivity in Oxygen Assisted Alcohol Cross-Coupling on Gold
journal, November 2010
- Xu, Bingjun; Madix, Robert J.; Friend, Cynthia M.
- Journal of the American Chemical Society, Vol. 132, Issue 46
Exploiting basic principles to control the selectivity of the vapor phase catalytic oxidative cross-coupling of primary alcohols over nanoporous gold catalysts
journal, September 2015
- Wang, Lu-Cun; Stowers, Kara J.; Zugic, Branko
- Journal of Catalysis, Vol. 329
Noncovalent Bonding Controls Selectivity in Heterogeneous Catalysis: Coupling Reactions on Gold
journal, November 2016
- Karakalos, Stavros; Xu, Yunfei; Cheenicode Kabeer, Fairoja
- Journal of the American Chemical Society, Vol. 138, Issue 46
Ag/Au Mixed Sites Promote Oxidative Coupling of Methanol on the Alloy Surface
journal, March 2014
- Xu, Bingjun; Siler, Cassandra G. F.; Madix, Robert J.
- Chemistry - A European Journal, Vol. 20, Issue 16
Oxygen-Mediated Coupling of Alcohols over Nanoporous Gold Catalysts at Ambient Pressures
journal, January 2012
- Kosuda, Kathryn M.; Wittstock, Arne; Friend, Cynthia M.
- Angewandte Chemie International Edition, Vol. 51, Issue 7
Synthesis and Characterization of Hierarchical Porous Gold Materials
journal, February 2007
- Nyce, Gregory W.; Hayes, Joel R.; Hamza, Alex V.
- Chemistry of Materials, Vol. 19, Issue 3
Toward Controlled Modification of Nanoporous Gold. A Detailed Surface Science Study on Cleaning and Oxidation
journal, February 2012
- Schaefer, A.; Ragazzon, D.; Wittstock, A.
- The Journal of Physical Chemistry C, Vol. 116, Issue 7
Gold Catalysts: Nanoporous Gold Foams
journal, December 2006
- Zielasek, Volkmar; Jürgens, Birte; Schulz, Christian
- Angewandte Chemie International Edition, Vol. 45, Issue 48
Designing bimetallic catalysts for a green and sustainable future
journal, January 2012
- Sankar, Meenakshisundaram; Dimitratos, Nikolaos; Miedziak, Peter J.
- Chemical Society Reviews, Vol. 41, Issue 24
Hydrogen transfer pathways in the oxidation of methanol on Pd(100)
journal, April 1987
- Jorgensen, Scott W.; Madix, R. J.
- Surface Science, Vol. 183, Issue 1-2
Graphene-supported Au–Pd bimetallic nanoparticles with excellent catalytic performance in selective oxidation of methanol to methyl formate
journal, January 2013
- Wang, Ruiyi; Wu, Zhiwei; Chen, Chengmeng
- Chemical Communications, Vol. 49, Issue 74
Methyl Formate Formation from Methanol Oxidation Using Supported Gold–Palladium Nanoparticles
journal, December 2014
- Whiting, Gareth T.; Kondrat, Simon A.; Hammond, Ceri
- ACS Catalysis, Vol. 5, Issue 2
Remarkable Effect of Bimetallic Nanocluster Catalysts for Aerobic Oxidation of Alcohols: Combining Metals Changes the Activities and the Reaction Pathways to Aldehydes/Carboxylic Acids or Esters
journal, November 2010
- Kaizuka, Kosuke; Miyamura, Hiroyuki; Kobayashi, Shu̅
- Journal of the American Chemical Society, Vol. 132, Issue 43
The Effect of Size-Dependent Nanoparticle Energetics on Catalyst Sintering
journal, October 2002
- Campbell, C. T.
- Science, Vol. 298, Issue 5594
Solvent-free Oxidation of Primary Alcohols to Aldehydes using Supported Gold Catalysts
journal, September 2005
- Enache, Dan I.; Knight, David W.; Hutchings, Graham J.
- Catalysis Letters, Vol. 103, Issue 1-2
Clean preparation of methyl esters in one-step oxidative esterification of primary alcohols catalyzed by supported gold nanoparticles
journal, January 2009
- Oliveira, Rafael L.; Kiyohara, Pedro K.; Rossi, Liane M.
- Green Chemistry, Vol. 11, Issue 9
Aerobic Oxidative Esterification of Benzyl Alcohol and Acetaldehyde over Gold Supported on Nanostructured Ceria-Alumina Mixed Oxides
journal, February 2015
- Smolentseva, Elena; Costa, Vinícius V.; Cotta, Rafaela F.
- ChemCatChem, Vol. 7, Issue 6
Controlled Synthesis of Au Nanoparticles in the Nanocages of SBA-16: Improved Activity and Enhanced Recyclability for the Oxidative Esterification of Alcohols
journal, March 2012
- Hao, Yajuan; Chong, Yanzhu; Li, Shuru
- The Journal of Physical Chemistry C, Vol. 116, Issue 11
Efficient Synthesis of Amides and Esters from Alcohols under Aerobic Ambient Conditions Catalyzed by a Au/Mesoporous Al 2 O 3 Nanocatalyst
journal, April 2015
- Chng, Leng Leng; Yang, Jinhua; Ying, Jackie Y.
- ChemSusChem, Vol. 8, Issue 11
Oxygen activation on gold nanoparticles: separating the influence of particle size, particle shape and support interaction
journal, January 2010
- Boronat, Mercedes; Corma, Avelino
- Dalton Transactions, Vol. 39, Issue 36
Heterogeneous Gold-Based Catalysis for Green Chemistry: Low-Temperature CO Oxidation and Propene Oxidation
journal, June 2007
- Min, Byoung Koun; Friend, Cynthia M.
- Chemical Reviews, Vol. 107, Issue 6
Is Nanostructuring Sufficient To Get Catalytically Active Au?
journal, April 2016
- Klyushin, Alexander Yu.; Greiner, Mark T.; Huang, Xing
- ACS Catalysis, Vol. 6, Issue 5
Critical Size for O 2 Dissociation by Au Nanoparticles
journal, February 2009
- Roldán, Alberto; González, Silvia; Ricart, Josep Manel
- ChemPhysChem, Vol. 10, Issue 2
Nature and Role of Activated Molecular Oxygen Species at the Gold/Titania Interface in the Selective Oxidation of Alcohols
journal, August 2014
- Farnesi Camellone, Matteo; Marx, Dominik
- The Journal of Physical Chemistry C, Vol. 118, Issue 36
Aerobic oxidation of aldehydes under ambient conditions using supported gold nanoparticle catalysts
journal, January 2008
- Marsden, Charlotte; Taarning, Esben; Hansen, David
- Green Chem., Vol. 10, Issue 2
Rate-Acceleration in Gold-Nanocluster-Catalyzed Aerobic Oxidative Esterification Using 1,2- and 1,3-Diols and Their Derivatives
journal, November 2010
- Yasukawa, Tomohiro; Miyamura, Hiroyuki; Kobayashi, Shū
- Chemistry - An Asian Journal, Vol. 6, Issue 2
Aerobic Oxidation of Alcohols over Gold Catalysts: Role of Acid and Base
journal, October 2008
- Klitgaard, Søren K.; DeLa Riva, Andrew T.; Helveg, Stig
- Catalysis Letters, Vol. 126, Issue 3-4
Aerobic oxidative esterification of alcohols catalyzed by polymer-incarcerated gold nanoclusters under ambient conditions
journal, January 2010
- Miyamura, Hiroyuki; Yasukawa, Tomohiro; Kobayashi, Shū
- Green Chemistry, Vol. 12, Issue 5
Formation of Acetic Acid by Aqueous-Phase Oxidation of Ethanol with Air in the Presence of a Heterogeneous Gold Catalyst
journal, July 2006
- Christensen, Claus H.; Jørgensen, Betina; Rass-Hansen, Jeppe
- Angewandte Chemie International Edition, Vol. 45, Issue 28
Gold supported on a mesoporous CeO2 matrix as an efficient catalyst in the selective aerobic oxidation of aldehydes in the liquid phase
journal, January 2005
- Corma, Avelino; Domine, Marcelo E.
- Chemical Communications, Issue 32
Efficient Tandem Synthesis of Methyl Esters and Imines by Using Versatile Hydrotalcite-Supported Gold Nanoparticles
journal, August 2012
- Liu, Peng; Li, Can; Hensen, Emiel J. M.
- Chemistry - A European Journal, Vol. 18, Issue 38
van der Waals Interactions Determine Selectivity in Catalysis by Metallic Gold
journal, September 2014
- Rodriguez-Reyes, Juan Carlos F.; Siler, Cassandra G. F.; Liu, Wei
- Journal of the American Chemical Society, Vol. 136, Issue 38
Origin of the selectivity in the gold-mediated oxidation of benzyl alcohol
journal, August 2012
- Rodríguez-Reyes, Juan Carlos F.; Friend, Cynthia M.; Madix, Robert J.
- Surface Science, Vol. 606, Issue 15-16
Direct aerobic oxidation of primary alcohols to methyl esters catalyzed by a heterogeneous gold catalyst
journal, April 2007
- Nielsen, Inger S.; Taarning, Esben; Egeblad, Kresten
- Catalysis Letters, Vol. 116, Issue 1-2
N -Formylation of Amines via the Aerobic Oxidation of Methanol over Supported Gold Nanoparticles
journal, June 2009
- Ishida, Tamao; Haruta, Masatake
- ChemSusChem, Vol. 2, Issue 6
Oxidative Coupling of Alcohols and Amines over Bimetallic Unsupported Nanoporous Gold: Tailored Activity through Mechanistic Predictability
journal, November 2014
- Wichmann, Andre; Bäumer, Marcus; Wittstock, Arne
- ChemCatChem, Vol. 7, Issue 1
Selective Aerobic Oxidation of Methanol in the Coexistence of Amines by Nanoporous Gold Catalysts: Highly Efficient Synthesis of Formamides
journal, August 2013
- Tanaka, Shinya; Minato, Taketoshi; Ito, Eisuke
- Chemistry - A European Journal, Vol. 19, Issue 36
Gold Supported on Nanocrystalline β-Ga 2 O 3 as a Versatile Bifunctional Catalyst for Facile Oxidative Transformation of Alcohols, Aldehydes, and Acetals into Esters
journal, August 2008
- Su, Fang-Zheng; Ni, Ji; Sun, Hao
- Chemistry - A European Journal, Vol. 14, Issue 24
A Collaborative Effect between Gold and a Support Induces the Selective Oxidation of Alcohols
journal, June 2005
- Abad, Alberto; Concepción, Patricia; Corma, Avelino
- Angewandte Chemie International Edition, Vol. 44, Issue 26
Surface-Mediated Self-Coupling of Ethanol on Gold
journal, April 2009
- Liu, Xiaoying; Xu, Bingjun; Haubrich, Jan
- Journal of the American Chemical Society, Vol. 131, Issue 16
Selective oxidation of alcohol over supported gold catalysts: methyl glycolate formation from ethylene glycol and methanol
journal, September 2006
- Hayashi, T.; Inagaki, T.; Itayama, N.
- Catalysis Today, Vol. 117, Issue 1-3
Oxidative coupling of alcohols on gold: Insights from experiments and theory
journal, January 2011
- Xu, Bingjun; Friend, Cynthia M.
- Faraday Discussions, Vol. 152
Selective Oxidation of Ethanol to Acetaldehyde on Gold
journal, December 2008
- Gong, Jinlong; Mullins, C. Buddie
- Journal of the American Chemical Society, Vol. 130, Issue 49
Selective Oxidation of Propanol on Au(111): Mechanistic Insights into Aerobic Oxidation of Alcohols
journal, December 2008
- Gong, Jinlong; Flaherty, David W.; Yan, Ting
- ChemPhysChem, Vol. 9, Issue 17
Oxidation of alcohols using supported gold and gold–palladium nanoparticles
journal, January 2010
- Meenakshisundaram, Sankar; Nowicka, Ewa; Miedziak, Peter J.
- Faraday Discuss., Vol. 145
Predicting Gold-Mediated Catalytic Oxidative-Coupling Reactions from Single Crystal Studies
journal, December 2013
- Xu, Bingjun; Madix, Robert J.; Friend, Cynthia M.
- Accounts of Chemical Research, Vol. 47, Issue 3
Acid-base reactions on solid surfaces: The reactions of HCOOH, H2CO, and HCOOCH3 with oxygen on Ag(110)
journal, April 1980
- Barteau, M. A.; Bowker, M.; Madix, R. J.
- Surface Science, Vol. 94, Issue 2-3
A study of the relative brönsted acidities of surface complexes on Ag(110)
journal, August 1982
- Barteau, M. A.; Madix, R. J.
- Surface Science, Vol. 120, Issue 2
Magnesia-supported gold nanoparticles as efficient catalysts for oxidative esterification of aldehydes or alcohols with methanol to methyl esters
journal, September 2014
- Wan, Xiaoyue; Deng, Weiping; Zhang, Qinghong
- Catalysis Today, Vol. 233
The oxidation of ethanol on Cu(110) and Ag(110) catalysts
journal, May 1978
- Wachs, Israel E.; Madix, Robert J.
- Applications of Surface Science, Vol. 1, Issue 3
The oxidation of methanol on a silver (110) catalyst
journal, September 1978
- Wachs, Israel E.; Madix, Robert J.
- Surface Science, Vol. 76, Issue 2, p. 531-558
Reactivity of Unsaturated Linear C6Hydrocarbons on Pd(111) and H(D)/Pd(111)
journal, August 1998
- Vasquez, Natividad; Madix, R. J.
- Journal of Catalysis, Vol. 178, Issue 1
Mechanistic Insights on the Hydrogenation of α,β-Unsaturated Ketones and Aldehydes to Unsaturated Alcohols over Metal Catalysts
journal, March 2012
- Ide, Matthew S.; Hao, Bing; Neurock, Matthew
- ACS Catalysis, Vol. 2, Issue 4
Decarbonylation and hydrogenation reactions of allyl alcohol and acrolein on Pd(110)
journal, November 1994
- Shekhar, Ratna; Barteau, Mark A.
- Surface Science, Vol. 319, Issue 3
Oxygen-Activated Combustion of Alkenes on the Pd(100) Surface
journal, May 1995
- Guo, Xing-Cai; Madix, Robert J.
- Journal of the American Chemical Society, Vol. 117, Issue 20
Partial Oxidation of Propene on Oxygen-Covered Au(111)
journal, August 2006
- Deng, Xingyi; Min, Byoung Koun; Liu, Xiaoying
- The Journal of Physical Chemistry B, Vol. 110, Issue 32
Selective Oxidation of Styrene on an Oxygen-Covered Au(111)
journal, December 2005
- Deng, Xingyi; Friend, Cynthia M.
- Journal of the American Chemical Society, Vol. 127, Issue 49
Control of selectivity in allylic alcohol oxidation on gold surfaces: the role of oxygen adatoms and hydroxyl species
journal, January 2015
- Mullen, Gregory M.; Zhang, Liang; Evans, Edward J.
- Physical Chemistry Chemical Physics, Vol. 17, Issue 6
Oxygen and Hydroxyl Species Induce Multiple Reaction Pathways for the Partial Oxidation of Allyl Alcohol on Gold
journal, April 2014
- Mullen, Gregory M.; Zhang, Liang; Evans, Edward J.
- Journal of the American Chemical Society, Vol. 136, Issue 17
Supported gold nanoparticles for aerobic, solventless oxidation of allylic alcohols
journal, January 2007
- Abad, Alberto; Corma, Avelino; García, Hermenegildo
- Pure and Applied Chemistry, Vol. 79, Issue 11
Highly Selective Acylation of Dimethylamine Mediated by Oxygen Atoms on Metallic Gold Surfaces
journal, December 2009
- Xu, Bingjun; Zhou, Ling; Madix, Robert J.
- Angewandte Chemie International Edition, Vol. 49, Issue 2
A Pathway for NH Addition to Styrene Promoted by Gold
journal, October 2006
- Deng, Xingyi; Baker, Thomas A.; Friend, Cynthia M.
- Angewandte Chemie International Edition, Vol. 45, Issue 42
Cleavage of NH bonds by active oxygen on Ag(110): II. Selective oxidation of ethylamine to acetonitrile
journal, February 1990
- Thornburg, D. M.; Madix, R. J.
- Surface Science, Vol. 226, Issue 1-2, p. 61-76
Cleavage of N-H bonds by active oxygen on Ag(110): I. Ammonia
journal, October 1989
- Thornburg, D. M.; Madix, R. J.
- Surface Science, Vol. 220, Issue 2-3, p. 268-294
One-pot synthesis of amides by aerobic oxidative coupling of alcohols or aldehydes with amines using supported gold and base as catalysts
journal, January 2012
- Kegnæs, Søren; Mielby, Jerrik; Mentzel, Uffe V.
- Chemical Communications, Vol. 48, Issue 18
Oxidations of amines with molecular oxygen using bifunctional gold–titania catalysts
journal, January 2008
- Klitgaard, Søren K.; Egeblad, Kresten; Mentzel, Uffe V.
- Green Chemistry, Vol. 10, Issue 4
Aerobic oxidative transformation of primary alcohols and amines to amides promoted by a hydroxyapatite-supported gold catalyst in water
journal, January 2014
- Wang, Wentao; Cong, Yu; Zhang, Leilei
- Tetrahedron Letters, Vol. 55, Issue 1
Aerobic oxidative coupling of alcohols and amines over Au–Pd/resin in water: Au/Pd molar ratios switch the reaction pathways to amides or imines
journal, January 2013
- Zhang, Leilei; Wang, Wentao; Wang, Aiqin
- Green Chemistry, Vol. 15, Issue 10
Direct Amidation from Alcohols and Amines through a Tandem Oxidation Process Catalyzed by Heterogeneous‐Polymer‐Incarcerated Gold Nanoparticles under Aerobic Conditions
journal, September 2013
- Soulé, Jean‐François; Miyamura, Hiroyuki; Kobayashi, Shū
- Chemistry – An Asian Journal, Vol. 8, Issue 11
Powerful Amide Synthesis from Alcohols and Amines under Aerobic Conditions Catalyzed by Gold or Gold/Iron, -Nickel or -Cobalt Nanoparticles
journal, November 2011
- Soulé, Jean-François; Miyamura, Hiroyuki; Kobayashi, Shu̅
- Journal of the American Chemical Society, Vol. 133, Issue 46
Highly Efficient Amide Synthesis from Alcohols and Amines by Virtue of a Water-Soluble Gold/DNA Catalyst
journal, August 2011
- Wang, Ye; Zhu, Dapeng; Tang, Lin
- Angewandte Chemie International Edition, Vol. 50, Issue 38
Adsorption and Reaction of Aldehydes on Pd Surfaces
journal, October 1997
- Shekhar, Ratna; Barteau, Mark A.; Plank, Russell V.
- The Journal of Physical Chemistry B, Vol. 101, Issue 40
Volcano-like Behavior of Au-Pd Core-shell Nanoparticles in the Selective Oxidation of Alcohols
journal, July 2014
- Silva, Tiago A. G.; Teixeira-Neto, Erico; López, Núria
- Scientific Reports, Vol. 4, Issue 1
Non-nanogold catalyzed aerobic oxidation of secondary amines to imines
journal, January 2007
- Zhu, Bolin; Angelici, Robert J.
- Chemical Communications, Issue 21
Aerobic oxidation of amines to imines catalyzed by bulk gold powder and by alumina-supported gold
journal, November 2008
- Zhu, Bolin; Lazar, Mihaela; Trewyn, Brian G.
- Journal of Catalysis, Vol. 260, Issue 1
Gold Metal-Catalyzed Reactions of Isocyanides with Primary Amines and Oxygen: Analogies with Reactions of Isocyanides in Transition Metal Complexes
journal, August 2006
- Lazar, Mihaela; Angelici, Robert J.
- Journal of the American Chemical Society, Vol. 128, Issue 32
Bulk gold (non-nanogold) catalysis of aerobic oxidations of amines, isocyanides, carbon monoxide, and carbene precursors
journal, January 2013
- Angelici, Robert J.
- Catal. Sci. Technol., Vol. 3, Issue 2
Non-Nanogold Catalysis of Carbon Monoxide Oxidative Amination
journal, October 2006
- Zhu, Bolin; Angelici, Robert J.
- Journal of the American Chemical Society, Vol. 128, Issue 45
Dimethyl Carbonate: An Eco-Friendly Solvent in Ruthenium-Catalyzed Olefin Metathesis Transformations
journal, October 2008
- Miao, Xiaowei; Fischmeister, Cédric; Bruneau, Christian
- ChemSusChem, Vol. 1, Issue 10
Properties of a potential biofuel obtained from soybean oil by transmethylation with dimethyl carbonate
journal, March 2007
- Fabbri, Daniele; Bevoni, Valerio; Notari, Marcello
- Fuel, Vol. 86, Issue 5-6
The Chemistry of Dimethyl Carbonate
journal, September 2002
- Tundo, Pietro; Selva, Maurizio
- Accounts of Chemical Research, Vol. 35, Issue 9
Catalysts, mechanisms and industrial processes for the dimethylcarbonate synthesis
journal, February 2010
- Keller, Nicolas; Rebmann, Guillaume; Keller, Valérie
- Journal of Molecular Catalysis A: Chemical, Vol. 317, Issue 1-2
Works referencing / citing this record:
Direct aerobic oxidation of alcohols into esters catalyzed by carbon nanotube–gold nanohybrids
journal, January 2019
- Gopi, Elumalai; Gravel, Edmond; Doris, Eric
- Nanoscale Advances, Vol. 1, Issue 3
Bulk gold catalyzes hydride transfer in the Cannizzaro and related reactions
journal, January 2019
- Fecteau, Kristopher M.; Gould, Ian R.; Williams, Lynda B.
- New Journal of Chemistry, Vol. 43, Issue 48
Metal-Support Cooperative Effects in Au/VPO for the Aerobic Oxidation of Benzyl Alcohol to Benzyl Benzoate
journal, February 2019
- Campisi, Sebastiano; Ferri, Michele; Chan-Thaw, Carine
- Nanomaterials, Vol. 9, Issue 2
Aerobic Methanol Oxidation over Unsupported Nanoporous Gold: The Influence of an Added Base
journal, May 2019
- Lackmann, Anastasia; Mahr, Christoph; Rosenauer, Andreas
- Catalysts, Vol. 9, Issue 5
Perspectives on the design of nanoparticle systems for catalysis
journal, January 2018
- Friend, Cynthia M.; Xu, Fang
- Faraday Discussions, Vol. 208
CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides
journal, January 2018
- Kataoka, Kengo; Wachi, Keiju; Jin, Xiongjie
- Chemical Science, Vol. 9, Issue 21
A comparative study of secondary depolymerization methods on oxidized lignins
journal, January 2019
- Song, Yang; Motagamwala, Ali Hussain; Karlen, Steven D.
- Green Chemistry, Vol. 21, Issue 14
Metal Catalysts for Heterogeneous Catalysis: From Single Atoms to Nanoclusters and Nanoparticles
journal, April 2018
- Liu, Lichen; Corma, Avelino
- Chemical Reviews, Vol. 118, Issue 10
Metal-Support Cooperative Effects in Au/VPO for the Aerobic Oxidation of Benzyl Alcohol to Benzyl Benzoate
journal, February 2019
- Campisi, Sebastiano; Ferri, Michele; Chan-Thaw, Carine
- Nanomaterials, Vol. 9, Issue 2