Comparative CO 2 Hydrogenation Catalysis with MACHO-type Manganese Complexes

Hert, Clayton M.; Curley, Julia B.; Kelley, Steven P.; Hazari, Nilay; Bernskoetter, Wesley H.

doi:10.1021/acs.organomet.2c00295

Comparative CO ₂ Hydrogenation Catalysis with MACHO-type Manganese Complexes

Journal Article · Tue Sep 27 00:00:00 EDT 2022 · Organometallics

DOI:https://doi.org/10.1021/acs.organomet.2c00295· OSTI ID:1978212

Hert, Clayton M. ^[1]; Curley, Julia B. ^[2]; ^[3]; ^[2]; ^[3]

The Department of Chemistry, The University of Missouri, Columbia, Missouri 65211, United States; OSTI
The Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, United States
The Department of Chemistry, The University of Missouri, Columbia, Missouri 65211, United States

Not provided.

Research Organization:: Univ. of Missouri, Columbia, MO (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0018222

OSTI ID:: 1978212

Journal Information:: Organometallics, Journal Name: Organometallics Journal Issue: 22 Vol. 41; ISSN 0276-7333

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

References (67)

Integrated CO ₂ Capture and Conversion to Formate and Methanol: Connecting Two Threads Kar, Sayan; Goeppert, Alain; Prakash, G. K. Surya Accounts of Chemical Research, Vol. 52, Issue 10 https://doi.org/10.1021/acs.accounts.9b00324	journal	September 2019
Mechanism of iron complexes catalyzed in the N-formylation of amines with CO₂ and H₂: the superior performance of N–H ligand methylated complexes Shen, Xinyu; Wang, Wenjuan; Wang, Qiong Physical Chemistry Chemical Physics, Vol. 23, Issue 31 https://doi.org/10.1039/D1CP00608H	journal	January 2021
Catalytic Upgrading of Ethanol to n -Butanol via Manganese-Mediated Guerbet Reaction Kulkarni, Naveen V.; Brennessel, William W.; Jones, William D. ACS Catalysis, Vol. 8, Issue 2 https://doi.org/10.1021/acscatal.7b03653	journal	January 2018
Aliphatic Mn–PNP complexes for the CO ₂ hydrogenation reaction: a base free mechanism Rawat, Kuber Singh; Pathak, Biswarup Catalysis Science & Technology, Vol. 7, Issue 15 https://doi.org/10.1039/C7CY00737J	journal	January 2017
Hydrogenation of CO₂ to methanol catalyzed by a manganese pincer complex: insights into the mechanism and solvent effect Zhang, Lin; Pu, Min; Lei, Ming Dalton Transactions, Vol. 50, Issue 21 https://doi.org/10.1039/D1DT01243F	journal	January 2021
Additive‐Free Isomerization of Allylic Alcohols to Ketones with a Cobalt PNP Pincer Catalyst Spiegelberg, Brian; Dell'Acqua, Andrea; Xia, Tian Chemistry – A European Journal, Vol. 25, Issue 33 https://doi.org/10.1002/chem.201901148	journal	April 2019
Iron catalyzed CO ₂ hydrogenation to formate enhanced by Lewis acid co-catalysts Zhang, Yuanyuan; MacIntosh, Alex D.; Wong, Janice L. Chemical Science, Vol. 6, Issue 7 https://doi.org/10.1039/C5SC01467K	journal	January 2015
Carbon dioxide hydrogenation catalysed by well-defined Mn( i ) PNP pincer hydride complexes Bertini, Federica; Glatz, Mathias; Gorgas, Nikolaus Chemical Science, Vol. 8, Issue 7 https://doi.org/10.1039/C7SC00209B	journal	January 2017
Selective Catalytic Hydrogenations of Nitriles, Ketones, and Aldehydes by Well-Defined Manganese Pincer Complexes Elangovan, Saravanakumar; Topf, Christoph; Fischer, Steffen Journal of the American Chemical Society, Vol. 138, Issue 28 https://doi.org/10.1021/jacs.6b03709	journal	July 2016
Metal-ligand bifunctional based Mn-catalysts for CO2 hydrogenation reaction Singh Rawat, Kuber; Garg, Priyanka; Bhauriyal, Preeti Molecular Catalysis, Vol. 468 https://doi.org/10.1016/j.mcat.2019.02.017	journal	May 2019
CO ₂ activation by manganese pincer complexes through different modes of metal–ligand cooperation Kumar, Amit; Daw, Prosenjit; Espinosa-Jalapa, Noel Angel Dalton Transactions, Vol. 48, Issue 39 https://doi.org/10.1039/C9DT03088C	journal	January 2019
Enabling Two-Electron Pathways with Iron and Cobalt: From Ligand Design to Catalytic Applications Arevalo, Rebeca; Chirik, Paul J. Journal of the American Chemical Society, Vol. 141, Issue 23 https://doi.org/10.1021/jacs.9b03337	journal	May 2019
Correlations of NHN hydrogen bond energy with geometry and¹H NMR chemical shift difference of NH protons for aniline complexes Tupikina, E. Yu.; Sigalov, M.; Shenderovich, I. G. The Journal of Chemical Physics, Vol. 150, Issue 11 https://doi.org/10.1063/1.5090180	journal	March 2019
Effective Pincer Cobalt Precatalysts for Lewis Acid Assisted CO ₂ Hydrogenation Spentzos, Ariana Z.; Barnes, Charles L.; Bernskoetter, Wesley H. Inorganic Chemistry, Vol. 55, Issue 16 https://doi.org/10.1021/acs.inorgchem.6b01454	journal	July 2016
Flexible proton-responsive ligand-based Mn( i ) complexes for CO ₂ hydrogenation: a DFT study Rawat, Kuber Singh; Pathak, Biswarup Physical Chemistry Chemical Physics, Vol. 20, Issue 18 https://doi.org/10.1039/C7CP08637G	journal	January 2018
Selective Iron-Catalyzed N -Formylation of Amines using Dihydrogen and Carbon Dioxide Jayarathne, Upul; Hazari, Nilay; Bernskoetter, Wesley H. ACS Catalysis, Vol. 8, Issue 2 https://doi.org/10.1021/acscatal.7b03834	journal	January 2018
Main Group Lewis Acid-Mediated Transformations of Transition-Metal Hydride Complexes Maity, Ayan; Teets, Thomas S. Chemical Reviews, Vol. 116, Issue 15 https://doi.org/10.1021/acs.chemrev.6b00034	journal	May 2016
Reversible Hydrogenation of Carbon Dioxide to Formic Acid and Methanol: Lewis Acid Enhancement of Base Metal Catalysts Bernskoetter, Wesley H.; Hazari, Nilay Accounts of Chemical Research, Vol. 50, Issue 4 https://doi.org/10.1021/acs.accounts.7b00039	journal	February 2017
Dihydrogen complexes as prototypes for the coordination chemistry of saturated molecules Kubas, G. J. Proceedings of the National Academy of Sciences, Vol. 104, Issue 17 https://doi.org/10.1073/pnas.0609707104	journal	April 2007
Advances in the Design of Heterogeneous Catalysts and Thermocatalytic Processes for CO ₂ Utilization De, Sudipta; Dokania, Abhay; Ramirez, Adrian ACS Catalysis, Vol. 10, Issue 23 https://doi.org/10.1021/acscatal.0c04273	journal	November 2020
Recent Advances in Carbon Dioxide Hydrogenation to Methanol via Heterogeneous Catalysis Jiang, Xiao; Nie, Xiaowa; Guo, Xinwen Chemical Reviews, Vol. 120, Issue 15 https://doi.org/10.1021/acs.chemrev.9b00723	journal	February 2020
Homogeneous Catalysis for Sustainable Energy: Hydrogen and Methanol Economies, Fuels from Biomass, and Related Topics Kumar, Amit; Daw, Prosenjit; Milstein, David Chemical Reviews, Vol. 122, Issue 1 https://doi.org/10.1021/acs.chemrev.1c00412	journal	November 2021
Manganese-Catalyzed Sequential Hydrogenation of CO ₂ to Methanol via Formamide Kar, Sayan; Goeppert, Alain; Kothandaraman, Jotheeswari ACS Catalysis, Vol. 7, Issue 9 https://doi.org/10.1021/acscatal.7b02066	journal	August 2017
Lewis Acid-Assisted Formic Acid Dehydrogenation Using a Pincer-Supported Iron Catalyst Bielinski, Elizabeth A.; Lagaditis, Paraskevi O.; Zhang, Yuanyuan Journal of the American Chemical Society, Vol. 136, Issue 29 https://doi.org/10.1021/ja505241x	journal	July 2014
Catalysis for the Valorization of Exhaust Carbon: from CO ₂ to Chemicals, Materials, and Fuels. Technological Use of CO ₂ Aresta, Michele; Dibenedetto, Angela; Angelini, Antonella Chemical Reviews, Vol. 114, Issue 3 https://doi.org/10.1021/cr4002758	journal	November 2013
Highly Active and Selective Manganese C=O Bond Hydrogenation Catalysts: The Importance of the Multidentate Ligand, the Ancillary Ligands, and the Oxidation State Kallmeier, Fabian; Irrgang, Torsten; Dietel, Thomas Angewandte Chemie International Edition, Vol. 55, Issue 39 https://doi.org/10.1002/anie.201606218	journal	August 2016
CO ₂ Hydrogenation to Formate and Methanol as an Alternative to Photo- and Electrochemical CO ₂ Reduction Wang, Wan-Hui; Himeda, Yuichiro; Muckerman, James T. Chemical Reviews, Vol. 115, Issue 23 https://doi.org/10.1021/acs.chemrev.5b00197	journal	August 2015
Manganese-Catalyzed Environmentally Benign Dehydrogenative Coupling of Alcohols and Amines to Form Aldimines and H ₂ : A Catalytic and Mechanistic Study Mukherjee, Arup; Nerush, Alexander; Leitus, Gregory Journal of the American Chemical Society, Vol. 138, Issue 13 https://doi.org/10.1021/jacs.5b13519	journal	March 2016
A computational study on ligand assisted vs. ligand participation mechanisms for CO ₂ hydrogenation: importance of bifunctional ligand based catalysts Mandal, Shyama Charan; Rawat, Kuber Singh; Pathak, Biswarup Physical Chemistry Chemical Physics, Vol. 21, Issue 7 https://doi.org/10.1039/C8CP06714G	journal	January 2019
Bio-Inspired Mn(I) Complexes for the Hydrogenation of CO ₂ to Formate and Formamide Dubey, Abhishek; Nencini, Luca; Fayzullin, Robert R. ACS Catalysis, Vol. 7, Issue 6 https://doi.org/10.1021/acscatal.7b00943	journal	May 2017
Iron-Based Catalysts for the Hydrogenation of Esters to Alcohols Chakraborty, Sumit; Dai, Huiguang; Bhattacharya, Papri Journal of the American Chemical Society, Vol. 136, Issue 22 https://doi.org/10.1021/ja504034q	journal	May 2014
Formic acid as a hydrogen storage material – development of homogeneous catalysts for selective hydrogen release Mellmann, Dörthe; Sponholz, Peter; Junge, Henrik Chemical Society Reviews, Vol. 45, Issue 14 https://doi.org/10.1039/C5CS00618J	journal	January 2016
Additive‐Free Formic Acid Dehydrogenation Using a Pincer‐Supported Iron Catalyst Curley, Julia B.; Bernskoetter, Wesley H.; Hazari, Nilay ChemCatChem, Vol. 12, Issue 7 https://doi.org/10.1002/cctc.202000066	journal	February 2020
Advances in Catalytic Enantioselective Fluorination, Mono-, Di-, and Trifluoromethylation, and Trifluoromethylthiolation Reactions Yang, Xiaoyu; Wu, Tao; Phipps, Robert J. Chemical Reviews, Vol. 115, Issue 2 https://doi.org/10.1021/cr500277b	journal	August 2014
The impact of Metal–Ligand Cooperation in Hydrogenation of Carbon Dioxide Catalyzed by Ruthenium PNP Pincer Filonenko, Georgy A.; Conley, Matthew P.; Copéret, Christophe ACS Catalysis, Vol. 3, Issue 11 https://doi.org/10.1021/cs4006869	journal	October 2013
Reversible 1,2-Addition of Water To Form a Nucleophilic Mn(I) Hydroxide Complex: A Thermodynamic and Reactivity Study Tondreau, Aaron M.; Michalczyk, Ryszard; Boncella, James M. Organometallics, Vol. 36, Issue 21 https://doi.org/10.1021/acs.organomet.7b00618	journal	September 2017
Hydride & dihydrogen complexes of earth abundant metals: structure, reactivity, and applications to catalysis Robinson, S. J. Connelly; Heinekey, D. M. Chemical Communications, Vol. 53, Issue 4 https://doi.org/10.1039/C6CC07529K	journal	January 2017
Homogeneous Catalysis by Cobalt and Manganese Pincer Complexes Mukherjee, Arup; Milstein, David ACS Catalysis, Vol. 8, Issue 12 https://doi.org/10.1021/acscatal.8b02869	journal	October 2018
Reversible hydrogenation of carbon dioxide to formic acid using a Mn-pincer complex in the presence of lysine Wei, Duo; Sang, Rui; Sponholz, Peter Nature Energy, Vol. 7, Issue 5 https://doi.org/10.1038/s41560-022-01019-4	journal	May 2022
Hydrogen energy future with formic acid: a renewable chemical hydrogen storage system Singh, Ashish Kumar; Singh, Suryabhan; Kumar, Abhinav Catalysis Science & Technology, Vol. 6, Issue 1 https://doi.org/10.1039/C5CY01276G	journal	January 2016
Influences of Bifunctional PNP-Pincer Ligands on Low Valent Cobalt Complexes Relevant to CO ₂ Hydrogenation Mills, Matthew R.; Barnes, Charles L.; Bernskoetter, Wesley H. Inorganic Chemistry, Vol. 57, Issue 3 https://doi.org/10.1021/acs.inorgchem.7b02931	journal	January 2018
Proton-Catalyzed Hydrogenation of a d ⁸ Ir(I) Complex Yields a trans Ir(III) Dihydride Findlater, Michael; Bernskoetter, Wesley H.; Brookhart, Maurice Journal of the American Chemical Society, Vol. 132, Issue 13 https://doi.org/10.1021/ja100168w	journal	April 2010
Iron, Cobalt, and Nickel Complexes Supported by a ^iPrPN^PhP Pincer Ligand Curley, Julia B.; Townsend, Tanya M.; Bernskoetter, Wesley H. Organometallics, Vol. 41, Issue 3 https://doi.org/10.1021/acs.organomet.1c00646	journal	January 2022
Clean hydrogen generation and storage strategies via CO 2 utilization into chemicals and fuels: A review Bahari, Nurazni Amat; Wan Isahak, Wan Nor Roslam; Masdar, Mohd Shahbudin International Journal of Energy Research, Vol. 43, Issue 10 https://doi.org/10.1002/er.4498	journal	March 2019
Catalytic Hydrogenation of Carbon Dioxide Using Ir(III)−Pincer Complexes Tanaka, Ryo; Yamashita, Makoto; Nozaki, Kyoko Journal of the American Chemical Society, Vol. 131, Issue 40 https://doi.org/10.1021/ja903574e	journal	October 2009
1,2-Addition of Formic or Oxalic Acid to ^– N{CH ₂ CH ₂ (PiPr ₂ )} ₂ -Supported Mn(I) Dicarbonyl Complexes and the Manganese-Mediated Decomposition of Formic Acid Tondreau, Aaron M.; Boncella, James M. Organometallics, Vol. 35, Issue 12 https://doi.org/10.1021/acs.organomet.6b00274	journal	June 2016
Ascendancy of Nitrogen Heterocycles in the Computationally Designed Mn(I)PNN Pincer Catalysts on the Hydrogenation of Carbon Dioxide to Methanol Avasare, Vidya D. Inorganic Chemistry, Vol. 61, Issue 4 https://doi.org/10.1021/acs.inorgchem.1c02689	journal	October 2021
Direct Hydrogenation of Amides to Alcohols and Amines under Mild Conditions Balaraman, Ekambaram; Gnanaprakasam, Boopathy; Shimon, Linda J. W. Journal of the American Chemical Society, Vol. 132, Issue 47, p. 16756-16758 https://doi.org/10.1021/ja1080019	journal	December 2010
Dual Coordination Modes of Ethylene-Linked NP2 Ligands in Cobalt(II) and Nickel(II) Iodides Dong, Qingchen; Rose, Michael J.; Wong, Wai-Yeung Inorganic Chemistry, Vol. 50, Issue 20 https://doi.org/10.1021/ic201213c	journal	September 2011
Manganese Pincer Complexes for the Base-Free, Acceptorless Dehydrogenative Coupling of Alcohols to Esters: Development, Scope, and Understanding Nguyen, Duc Hanh; Trivelli, Xavier; Capet, Frédéric ACS Catalysis, Vol. 7, Issue 3 https://doi.org/10.1021/acscatal.6b03554	journal	February 2017
Hydrogenation of CO ₂ to Methanol with Mn‐PNP‐Pincer Complexes in the Presence of Lewis Acids: the Formate Resting State Unleashed Kuß, David A.; Hölscher, Markus; Leitner, Walter ChemCatChem, Vol. 13, Issue 14 https://doi.org/10.1002/cctc.202100649	journal	May 2021
Catalytic Hydrogenation of CO₂ by Manganese Complexes: Role of π-Acceptor Ligands Rawat, Kuber Singh; Mahata, Arup; Choudhuri, Indrani The Journal of Physical Chemistry C, Vol. 120, Issue 30 https://doi.org/10.1021/acs.jpcc.6b05065	journal	July 2016
Benyzl Alcohol Dehydrogenative Coupling Catalyzed by Defined Mn and Re PNP Pincer Complexes - A Computational Mechanistic Study: Benyzl Alcohol Dehydrogenative Coupling Catalyzed by Defined Mn and Re PNP Pincer Complexes - A Computational Mechanistic Study Wei, Zhihong; de Aguirre, Adiran; Junge, Kathrin European Journal of Inorganic Chemistry, Vol. 2018, Issue 42 https://doi.org/10.1002/ejic.201800674	journal	November 2018
Bond Activation and Catalysis by Ruthenium Pincer Complexes Gunanathan, Chidambaram; Milstein, David Chemical Reviews, Vol. 114, Issue 24 https://doi.org/10.1021/cr5002782	journal	November 2014
Investigation of Hydrogenation of Formic Acid to Methanol using H ₂ or Formic Acid as a Hydrogen Source Tsurusaki, Akihiro; Murata, Kazuhisa; Onishi, Naoya ACS Catalysis, Vol. 7, Issue 2 https://doi.org/10.1021/acscatal.6b03194	journal	January 2017
Unraveling the catalytically preferential pathway between the direct and indirect hydrogenation of CO₂ to CH₃OH using N-heterocyclic carbene-based Mn(i) catalysts: a theoretical approach Das, Amitabha; Mandal, Shyama Charan; Pathak, Biswarup Catalysis Science & Technology, Vol. 11, Issue 4 https://doi.org/10.1039/D0CY02064H	journal	January 2021
Manganese-Catalyzed Upgrading of Ethanol into 1-Butanol Fu, Shaomin; Shao, Zhihui; Wang, Yujie Journal of the American Chemical Society, Vol. 139, Issue 34 https://doi.org/10.1021/jacs.7b05939	journal	August 2017
Metal-Nanoparticle-Catalyzed Hydrogen Generation from Formic Acid Li, Zhangpeng; Xu, Qiang Accounts of Chemical Research, Vol. 50, Issue 6 https://doi.org/10.1021/acs.accounts.7b00132	journal	May 2017
Homogeneous Catalysis for Sustainable Hydrogen Storage in Formic Acid and Alcohols Sordakis, Katerina; Tang, Conghui; Vogt, Lydia K. Chemical Reviews, Vol. 118, Issue 2 https://doi.org/10.1021/acs.chemrev.7b00182	journal	October 2017
Why Does Alkylation of the N–H Functionality within M/NH Bifunctional Noyori-Type Catalysts Lead to Turnover? Dub, Pavel A.; Scott, Brian L.; Gordon, John C. Journal of the American Chemical Society, Vol. 139, Issue 3 https://doi.org/10.1021/jacs.6b11666	journal	January 2017
Identifying the preferential pathways of CO₂ capture and hydrogenation to methanol over an Mn(i)–PNP catalyst: a computational study Mandal, Shyama Charan; Pathak, Biswarup Dalton Transactions, Vol. 50, Issue 27 https://doi.org/10.1039/D1DT01208H	journal	January 2021
Theoretical insights into CO ₂ hydrogenation to methanol by a Mn–PNP complex Mandal, Shyama Charan; Rawat, Kuber Singh; Nandi, Surajit Catalysis Science & Technology, Vol. 9, Issue 8 https://doi.org/10.1039/C9CY00114J	journal	January 2019
Unexpected concerted two-proton transfer for amination of formic acid to formamide catalysed by Mn bipyridinol complexes Yan, Xiuli; Ge, Hongyu; Yang, Xinzheng Catalysis Science & Technology, Vol. 8, Issue 22 https://doi.org/10.1039/C8CY01424H	journal	January 2018
Molecular hydrogen complexes: coordination of a .sigma. bond to transition metals Kubas, Gregory J. Accounts of Chemical Research, Vol. 21, Issue 3 https://doi.org/10.1021/ar00147a005	journal	March 1988
Unraveling the Effect of Aromatic Groups in Mn(I)NNN Pincer Complexes on Carbon Dioxide Activation Using Density Functional Study Parmar, Saurabh Vinod; Avasare, Vidya; Pal, Sourav Frontiers in Chemistry, Vol. 9 https://doi.org/10.3389/fchem.2021.778718	journal	November 2021
Control of Catalyst Isomers Using an N -Phenyl-Substituted RN(CH ₂ CH ₂ P ⁱ Pr ₂ ) ₂ Pincer Ligand in CO ₂ Hydrogenation and Formic Acid Dehydrogenation Curley, Julia B.; Hert, Clayton; Bernskoetter, Wesley H. Inorganic Chemistry, Vol. 61, Issue 1 https://doi.org/10.1021/acs.inorgchem.1c03372	journal	December 2021
Carbon Dioxide Hydrogenation to Formate Catalyzed by a Bench-Stable, Non-Pincer-Type Mn(I) Alkylcarbonyl Complex Kostera, Sylwia; Weber, Stefan; Peruzzini, Maurizio Organometallics, Vol. 40, Issue 9 https://doi.org/10.1021/acs.organomet.0c00710	journal	April 2021

Similar Records

Sequential Hydrogenation of CO ₂ to Methanol Using a Pincer Iron Catalyst

Journal Article · Mon Jul 29 00:00:00 EDT 2019 · Organometallics · OSTI ID:1612885

Catalytic Formic Acid Dehydrogenation and CO ₂ Hydrogenation Using Iron PN ^R P Pincer Complexes with Isonitrile Ligands

Journal Article · Tue Oct 16 00:00:00 EDT 2018 · Organometallics · OSTI ID:1612884

Iron Catalysts Supported by a PNP Ligand with an Additional Hemilabile Donor for CO ₂ Hydrogenation

Journal Article · Wed Sep 04 00:00:00 EDT 2024 · ACS Catalysis · OSTI ID:2577724

Related Subjects

Chemistry

Comparative CO 2 Hydrogenation Catalysis with MACHO-type Manganese Complexes

Citation Formats

References (67)

Similar Records

Related Subjects

Comparative CO ₂ Hydrogenation Catalysis with MACHO-type Manganese Complexes