Mesoporous cobalt/manganese oxide: a highly selective bifunctional catalyst for amine–imine transformations

Dutta, Biswanath; March, Seth; Achola, Laura; Sahoo, Sanjubala; He, Junkai; Shirazi Amin, Alireza; Wu, Yang; Poges, Shannon; Pamir Alpay, S.; Suib, Steven L.

doi:10.1039/c8gc00862k

Title: Mesoporous cobalt/manganese oxide: a highly selective bifunctional catalyst for amine–imine transformations

Journal Article · Mon Jan 01 00:00:00 EST 2018 · Green Chemistry

DOI:https://doi.org/10.1039/c8gc00862k· OSTI ID:1540053

^[1]; March, Seth ^[1]; Achola, Laura ^[1];

^[2]; He, Junkai ^[2]; Shirazi Amin, Alireza ^[1]; Wu, Yang ^[2]; Poges, Shannon ^[1];

^[2];

^[3]

Department of Chemistry; University of Connecticut; Storrs; USA
Institute of Material Science; University of Connecticut; Storrs; USA
Department of Chemistry; University of Connecticut; Storrs; USA; Institute of Material Science

Cobalt doped mesoporous manganese oxide: an excellent oxidative catalyst (for producing asymmetric imines with >98% selectivity) with significant reductive properties.

Cite

Export

Save

Research Organization:: Univ. of Connecticut, Storrs, CT (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: FG02-86ER13622

OSTI ID:: 1540053

Journal Information:: Green Chemistry, Vol. 20, Issue 14; ISSN 1463-9262

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

References (53)

The Chemistry of Imines. Layer, Robert W. Chemical Reviews, Vol. 63, Issue 5 https://doi.org/10.1021/cr60225a003	journal	October 1963
Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update Kobayashi, Shu̅; Mori, Yuichiro; Fossey, John S. Chemical Reviews, Vol. 111, Issue 4 https://doi.org/10.1021/cr100204f	journal	March 2011
Dynamic imine chemistry Belowich, Matthew E.; Stoddart, J. Fraser Chemical Society Reviews, Vol. 41, Issue 6 https://doi.org/10.1039/c2cs15305j	journal	January 2012
Catalytic Enantioselective Addition to Imines Kobayashi, Shū; Ishitani, Haruro Chemical Reviews, Vol. 99, Issue 5 https://doi.org/10.1021/cr980414z	journal	May 1999
Mild and convenient one pot synthesis of Schiff bases in the presence of P2O5/Al2O3 as new catalyst under solvent-free conditions Naeimi, Hossein; Salimi, Fariba; Rabiei, Khadigeh Journal of Molecular Catalysis A: Chemical, Vol. 260, Issue 1-2 https://doi.org/10.1016/j.molcata.2006.06.055	journal	December 2006
Recent Advances in Aerobic Oxidation of Alcohols and Amines to Imines Chen, Bo; Wang, Lianyue; Gao, Shuang ACS Catalysis, Vol. 5, Issue 10 https://doi.org/10.1021/acscatal.5b01479	journal	September 2015
Iridium( iii ) homo- and heterogeneous catalysed hydrogen borrowing C–N bond formation Wong, Chin M.; McBurney, Roy T.; Binding, Samantha C. Green Chemistry, Vol. 19, Issue 13 https://doi.org/10.1039/C7GC01007A	journal	January 2017
New Reactions of IBX: Oxidation of Nitrogen- and Sulfur-Containing Substrates To Afford Useful Synthetic Intermediates Nicolaou, K. C.; Mathison, Casey J. N.; Montagnon, Tamsyn Angewandte Chemie International Edition, Vol. 42, Issue 34 https://doi.org/10.1002/anie.200352076	journal	September 2003
A Biologically Inspired Cu ^I /Topaquinone-Like Co-Catalytic System for the Highly Atom-Economical Aerobic Oxidation of Primary Amines to Imines Largeron, Martine; Fleury, Maurice-Bernard Angewandte Chemie International Edition, Vol. 51, Issue 22 https://doi.org/10.1002/anie.201200587	journal	April 2012
Bioinspired Oxidation Catalysts Largeron, Martine; Fleury, Maurice-Bernard Science, Vol. 339, Issue 6115 https://doi.org/10.1126/science.1232220	journal	January 2013
Direct imine formation by oxidative coupling of alcohols and amines using supported manganese oxides under an air atmosphere Chen, Bo; Li, Jun; Dai, Wen Green Chemistry, Vol. 16, Issue 6 https://doi.org/10.1039/c4gc00336e	journal	January 2014
Gold Supported on Hydroxyapatite as a Versatile Multifunctional Catalyst for the Direct Tandem Synthesis of Imines and Oximes Sun, Hao; Su, Fang-Zheng; Ni, Ji Angewandte Chemie International Edition, Vol. 48, Issue 24 https://doi.org/10.1002/anie.200900802	journal	June 2009
Highly selective formation of imines catalyzed by silver nanoparticles supported on alumina Mielby, Jerrik; Poreddy, Raju; Engelbrekt, Christian Chinese Journal of Catalysis, Vol. 35, Issue 5 https://doi.org/10.1016/S1872-2067(14)60033-4	journal	May 2014
Direct and mild palladium-catalyzed aerobic oxidative synthesis of imines from alcohols and amines under ambient conditions Jiang, Lan; Jin, Luolu; Tian, Haiwen Chemical Communications, Vol. 47, Issue 38 https://doi.org/10.1039/c1cc14242a	journal	January 2011
Pt-Sn/γ-Al2O3-Catalyzed Highly Efficient Direct Synthesis of Secondary and Tertiary Amines and Imines He, Wei; Wang, Liandi; Sun, Chenglin Chemistry - A European Journal, Vol. 17, Issue 47 https://doi.org/10.1002/chem.201101725	journal	October 2011
Heterogeneously Catalyzed One-pot Synthesis of Aldimines from Primary Alcohols and Amines by Supported Ruthenium Hydroxides Kim, Jung Won; He, Jinling; Yamaguchi, Kazuya Chemistry Letters, Vol. 38, Issue 9 https://doi.org/10.1246/cl.2009.920	journal	September 2009
Tandem catalysis: Direct catalytic synthesis of imines from alcohols using manganese octahedral molecular sieves Sithambaram, S.; Kumar, R.; Son, Y. Journal of Catalysis, Vol. 253, Issue 2 https://doi.org/10.1016/j.jcat.2007.11.006	journal	January 2008
Sustainable iron-catalyzed direct imine formation by acceptorless dehydrogenative coupling of alcohols with amines Jaiswal, Garima; Landge, Vinod G.; Jagadeesan, Dinesh Green Chemistry, Vol. 18, Issue 11 https://doi.org/10.1039/C6GC00565A	journal	January 2016
Practical Aerobic Oxidations of Alcohols and Amines with Homogeneous Copper/TEMPO and Related Catalyst Systems Ryland, Bradford L.; Stahl, Shannon S. Angewandte Chemie International Edition, Vol. 53, Issue 34 https://doi.org/10.1002/anie.201403110	journal	July 2014
Redox Properties of CeO ₂ at Low Temperature: The Direct Synthesis of Imines from Alcohol and Amine Tamura, Masazumi; Tomishige, Keiichi Angewandte Chemie International Edition, Vol. 54, Issue 3 https://doi.org/10.1002/anie.201409601	journal	November 2014
Dehydrogenation and oxidative coupling of alcohol and amines catalyzed by organosilicon-supported TiO ₂ @PMHSIPN Wang, Hu; Zhang, Jin; Cui, Yu-Ming RSC Advances, Vol. 4, Issue 65 https://doi.org/10.1039/C4RA06685E	journal	January 2014
An Efficient, Visible Light Driven, Selective Oxidation of Aromatic Alcohols and Amines with O ₂ Using BiVO ₄ /g-C ₃ N ₄ Nanocomposite: A Systematic and Comprehensive Study toward the Development of a Photocatalytic Process Samanta, Subhajyoti; Khilari, Santimoy; Pradhan, Debabrata ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 3 https://doi.org/10.1021/acssuschemeng.6b02902	journal	January 2017
Use of an Iridium-Catalyzed Redox-Neutral Alcohol-Amine Coupling on Kilogram Scale for the Synthesis of a GlyT1 Inhibitor Berliner, Martin A.; Dubant, Stéphane P. A.; Makowski, Teresa Organic Process Research & Development, Vol. 15, Issue 5 https://doi.org/10.1021/op200174k	journal	September 2011
Graphite oxide as an efficient and durable metal-free catalyst for aerobic oxidative coupling of amines to imines Huang, Hai; Huang, Jun; Liu, Yong-Mei Green Chemistry, Vol. 14, Issue 4 https://doi.org/10.1039/c2gc16681j	journal	January 2012
Green Chemistry: Principles and Practice Anastas, Paul; Eghbali, Nicolas Chem. Soc. Rev., Vol. 39, Issue 1 https://doi.org/10.1039/B918763B	journal	January 2010
Bioinspired Aerobic Oxidation of Secondary Amines and Nitrogen Heterocycles with a Bifunctional Quinone Catalyst Wendlandt, Alison E.; Stahl, Shannon S. Journal of the American Chemical Society, Vol. 136, Issue 1 https://doi.org/10.1021/ja411692v	journal	December 2013
Heterogeneous mesoporous manganese/cobalt oxide catalysts for selective oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran Biswas, Sourav; Dutta, Biswanath; Mannodi-Kanakkithodi, Arun Chem. Commun., Vol. 53, Issue 86 https://doi.org/10.1039/C7CC06097A	journal	January 2017
Aerobic Oxidation of Amines to Imines by Cesium-Promoted Mesoporous Manganese Oxide Biswas, Sourav; Dutta, Biswanath; Mullick, Kankana ACS Catalysis, Vol. 5, Issue 7 https://doi.org/10.1021/acscatal.5b00325	journal	June 2015
Mesoporous Manganese Oxide Catalyzed Aerobic Oxidative Coupling of Anilines To Aromatic Azo Compounds Dutta, Biswanath; Biswas, Sourav; Sharma, Vinit Angewandte Chemie International Edition, Vol. 55, Issue 6 https://doi.org/10.1002/anie.201508223	journal	January 2016
Cross dehydrogenative coupling of N -aryltetrahydroisoquinolines (sp ³ C–H) with indoles (sp ² C–H) using a heterogeneous mesoporous manganese oxide catalyst Dutta, B.; Sharma, V.; Sassu, N. Green Chemistry, Vol. 19, Issue 22 https://doi.org/10.1039/C7GC01919J	journal	January 2017
Selective Alkane Oxidation by Manganese Oxide: Site Isolation of MnO _x Chains at the Surface of MnWO ₄ Nanorods Li, Xuan; Lunkenbein, Thomas; Pfeifer, Verena Angewandte Chemie International Edition, Vol. 55, Issue 12 https://doi.org/10.1002/anie.201510201	journal	February 2016
Structure, porosity, and redox in porous manganese oxide octahedral layer and molecular sieve materials Suib, Steven L. Journal of Materials Chemistry, Vol. 18, Issue 14 https://doi.org/10.1039/b714966m	journal	January 2008
Hydrogen Adsorption on Co Surfaces: A Density Functional Theory and Temperature Programmed Desorption Study van Helden, Pieter; van den Berg, Jan-Albert; Weststrate, Cornelis J. ACS Catalysis, Vol. 2, Issue 6 https://doi.org/10.1021/cs2006586	journal	April 2012
Effect of alkali and alkaline earth metal dopants on catalytic activity of mesoporous cobalt oxide evaluated using a model reaction Bingwa, Ndzondelelo; Bewana, Semakaleng; Ndolomingo, Matumuene Joe Applied Catalysis A: General, Vol. 555 https://doi.org/10.1016/j.apcata.2018.01.028	journal	April 2018
Importance of trivalency and the eg1 configuration in the photocatalytic oxidation of water by Mn and Co oxides Maitra, U.; Naidu, B. S.; Govindaraj, A. Proceedings of the National Academy of Sciences, Vol. 110, Issue 29 https://doi.org/10.1073/pnas.1310703110	journal	July 2013
Balancing the generation and elimination of reactive oxygen species Rodriguez, R.; Redman, R. Proceedings of the National Academy of Sciences, Vol. 102, Issue 9 https://doi.org/10.1073/pnas.0500367102	journal	February 2005
The involvement of superoxide anions in the nitro blue tetrazolium chloride reduction mediated by NADH and phenazine methosulfate Van Noorden, Cornelis J. F.; Butcher, Roger G. Analytical Biochemistry, Vol. 176, Issue 1 https://doi.org/10.1016/0003-2697(89)90288-1	journal	January 1989
Quantifying hydrogen peroxide in iron-containing solutions using leuco crystal violet Cohn, Corey A.; Pak, Aimee; Strongin, Daniel Geochemical Transactions, Vol. 6, Issue 3 https://doi.org/10.1186/1467-4866-6-47	journal	June 2005
Fluorescence probes used for detection of reactive oxygen species Gomes, Ana; Fernandes, Eduarda; Lima, José L. F. C. Journal of Biochemical and Biophysical Methods, Vol. 65, Issue 2-3 https://doi.org/10.1016/j.jbbm.2005.10.003	journal	December 2005
Antioxidant and radical scavenging properties of curcumin Ak, Tuba; Gülçin, İlhami Chemico-Biological Interactions, Vol. 174, Issue 1 https://doi.org/10.1016/j.cbi.2008.05.003	journal	July 2008
Detection and analysis of reactive oxygen species (ROS) generated by nano-sized TiO2 powder under ultrasonic irradiation and application in sonocatalytic degradation of organic dyes Wang, Jun; Guo, Yuwei; Liu, Bin Ultrasonics Sonochemistry, Vol. 18, Issue 1 https://doi.org/10.1016/j.ultsonch.2010.05.002	journal	January 2011
Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Kresse, G.; Furthmüller, J. Physical Review B, Vol. 54, Issue 16, p. 11169-11186 https://doi.org/10.1103/PhysRevB.54.11169	journal	October 1996
Efficiency of ab-initio total energy calculations for metals and semiconductors using a plane-wave basis set Kresse, G.; Furthmüller, J. Computational Materials Science, Vol. 6, Issue 1, p. 15-50 https://doi.org/10.1016/0927-0256(96)00008-0	journal	July 1996
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
Electron-energy-loss spectra and the structural stability of nickel oxide: An LSDA+U study Dudarev, S. L.; Botton, G. A.; Savrasov, S. Y. Physical Review B, Vol. 57, Issue 3, p. 1505-1509 https://doi.org/10.1103/PhysRevB.57.1505	journal	January 1998
Mesoporous Manganese Oxide Catalyzed Aerobic Oxidative Coupling of Anilines To Aromatic Azo Compounds Dutta, Biswanath; Biswas, Sourav; Sharma, Vinit Angewandte Chemie, Vol. 128, Issue 6 https://doi.org/10.1002/ange.201508223	journal	January 2016
New Reactions of IBX: Oxidation of Nitrogen- and Sulfur-Containing Substrates To Afford Useful Synthetic Intermediates Nicolaou, K. C.; Mathison, Casey J. N.; Montagnon, Tamsyn Angewandte Chemie, Vol. 115, Issue 34 https://doi.org/10.1002/ange.200352076	journal	September 2003
Gold Supported on Hydroxyapatite as a Versatile Multifunctional Catalyst for the Direct Tandem Synthesis of Imines and Oximes Sun, Hao; Su, Fang-Zheng; Ni, Ji Angewandte Chemie, Vol. 121, Issue 24 https://doi.org/10.1002/ange.200900802	journal	June 2009
Voltage- and time-dependent valence state transition in cobalt oxide catalysts during the oxygen evolution reaction Zhou, Jing; Zhang, Linjuan; Huang, Yu-Cheng Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-020-15925-2	journal	April 2020
High-resolution X-ray luminescence extension imaging Ou, Xiangyu; Qin, Xian; Huang, Bolong Nature, Vol. 590, Issue 7846 https://doi.org/10.1038/s41586-021-03251-6	journal	February 2021
A Biologically Inspired Cu ^I /Topaquinone-Like Co-Catalytic System for the Highly Atom-Economical Aerobic Oxidation of Primary Amines to Imines Largeron, Martine; Fleury, Maurice-Bernard Angewandte Chemie, Vol. 124, Issue 22 https://doi.org/10.1002/ange.201200587	journal	April 2012
New Reactions of IBX: Oxidation of Nitrogen- and Sulfur-Contaning Substrates to Afford Useful Synthetic Intermediates. Nicolaou, K. C.; Mathison, Casey J. N.; Montagnon, Tamsyn ChemInform, Vol. 34, Issue 50 https://doi.org/10.1002/chin.200350058	journal	December 2003
Redox Properties of CeO ₂ at Low Temperature: The Direct Synthesis of Imines from Alcohol and Amine Tamura, Masazumi; Tomishige, Keiichi Angewandte Chemie, Vol. 127, Issue 3 https://doi.org/10.1002/ange.201409601	journal	November 2014

Cited By (3)

Aerobic Self‐Esterification of Alcohols Assisted by Mesoporous Manganese and Cobalt Oxide Moharreri, Ehsan; Biswas, Sourav; Deljoo, Bahareh ChemCatChem, Vol. 11, Issue 15 https://doi.org/10.1002/cctc.201900704	journal	June 2019
Covalent Triazine Frameworks as Metal Free Catalysts for the Oxidative Coupling of Amines to Imines Zheng, He; Shi, Song; Wang, Xinhong ChemistrySelect, Vol. 4, Issue 17 https://doi.org/10.1002/slct.201901272	journal	May 2019
Polyoxometalates as bifunctional templates: engineering metal oxides with mesopores and reactive surfaces for catalysis Leng, Yan; Liu, Jixing; Zhang, Zihao Journal of Materials Chemistry A, Vol. 7, Issue 48 https://doi.org/10.1039/c9ta09614k	journal	January 2019

Similar Records

Mesoporous cobalt/manganese oxide: a highly selective bifunctional catalyst for amine–imine transformations

Journal Article · Mon Jan 01 00:00:00 EST 2018 · Green Chemistry · OSTI ID:1540053

Dutta, Biswanath; March, Seth; Achola, Laura; +7 more

Heterogeneous mesoporous manganese/cobalt oxide catalysts for selective oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran

Journal Article · Sun Jan 01 00:00:00 EST 2017 · ChemComm · OSTI ID:1540053

Biswas, Sourav; Dutta, Biswanath; Mannodi-Kanakkithodi, Arun; +4 more

Aerobic oxidative coupling of amines to imines by mesoporous copper aluminum mixed metal oxides via generation of Reactive Oxygen Species (ROS)

Journal Article · Thu Feb 21 00:00:00 EST 2019 · Applied Catalysis B: Environmental · OSTI ID:1540053

Dissanayake, Deepamali; Achola, Laura A.; Kerns, Peter; +4 more

Related Subjects

Chemistry
Science & Technology - Other Topics

Title: Mesoporous cobalt/manganese oxide: a highly selective bifunctional catalyst for amine–imine transformations

Citation Formats

References (53)

Cited By (3)

Similar Records

Related Subjects