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:1598153

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

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

^[1];

^[1]

Univ. of Connecticut, Storrs, CT (United States)

Here, we discuss a heterogeneous catalytic protocol using cobalt doped mesoporous manganese oxide for amine–alcohol cross-coupling to selectively produce symmetric or asymmetric imines. Thorough investigations on the surface chemistry and physical properties of the material revealed its outstanding oxidation–reduction properties and reaction mechanism which was supported by quantum mechanical calculations done by using density functional theory (DFT).

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

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

Grant/Contract Number:: FG02-86ER13622

OSTI ID:: 1598153

Alternate ID(s):: OSTI ID: 1454376

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

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 31 works

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References (52)

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
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
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
Bioinspired Oxidation Catalysts Largeron, Martine; Fleury, Maurice-Bernard Science, Vol. 339, Issue 6115 https://doi.org/10.1126/science.1232220	journal	January 2013
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
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
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
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
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
Catalytic Enantioselective Addition to Imines Kobayashi, Shū; Ishitani, Haruro Chemical Reviews, Vol. 99, Issue 5 https://doi.org/10.1021/cr980414z	journal	May 1999
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
The Chemistry of Imines. Layer, Robert W. Chemical Reviews, Vol. 63, Issue 5 https://doi.org/10.1021/cr60225a003	journal	October 1963
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
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

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