CO2 hydrogenation catalyzed by iridium complexes with a proton-responsive ligand

Onishi, Naoya; Xu, Shaoan; Manaka, Yuichi; Suna, Yuki; Wang, Wan -Hui; Muckerman, James T.; Fujita, Etsuko; Himeda, Yuichiro

doi:10.1021/ic502904q

Title: CO₂ hydrogenation catalyzed by iridium complexes with a proton-responsive ligand

Journal Article · Wed Feb 18 00:00:00 EST 2015 · Inorganic Chemistry

DOI:https://doi.org/10.1021/ic502904q· OSTI ID:1182536

Onishi, Naoya ^[1]; Xu, Shaoan ^[1]; Manaka, Yuichi ^[2]; Suna, Yuki ^[2]; Wang, Wan -Hui ^[2]; Muckerman, James T. ^[3]; Fujita, Etsuko ^[3]; Himeda, Yuichiro ^[1]

National Institute of Advanced Industrial Science and Technology, Ibaraki (Japan); Japan Science and Technology Agency, Saitama (Japan)
National Institute of Advanced Industrial Science and Technology, Ibaraki (Japan)
Brookhaven National Lab. (BNL), Upton, NY (United States)

In this study, the catalytic cycle for the production of formic acid by CO₂ hydrogenation and the reverse reaction has received renewed attention because they are viewed as offering a viable scheme for hydrogen storage and release. In this Forum Article, CO₂ hydrogenation catalyzed by iridium complexes bearing N^N-bidentate ligands is reported. We describe how a ligand containing hydroxyl groups as proton-responsive substituents enhances catalytic performance by an electronic effect of the oxyanions and a pendent-base effect through secondary coordination sphere interaction. In particular, [(Cp*IrCl)₂(TH2BPM)]Cl₂ (Cp* = pentamethyl cyclopentadienyl, TH2BPM = 4,4',6,6'-tetrahydroxy-2,2'-bipyrimidine) promotes enormously the catalytic hydrogenation of CO₂ by these synergistic effects under atmospheric pressure and at room temperature. Additionally, newly designed complexes with azole-type ligands are applied to CO₂ hydrogenation. The catalytic efficiencies of the azole-type complexes are much higher than that of the unsubstituted bipyridine complex [Cp*Ir(bpy)(OH₂)]SO₄. Furthermore, the introduction of one or more hydroxyl groups into ligands such as 2-pyrazolyl-6-hydroxypyridine, 2-pyrazolyl-4,6-dihydroxyl pyrimidine, and 4-pyrazolyl-2,6-dihydroxyl pyrimidine enhanced catalytic activity. It is clear that the incorporation of electron-donating hydroxyl groups into proton-responsive ligands is effective for promoting the hydrogenation of CO₂.

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Research Organization:: Brookhaven National Laboratory (BNL), Upton, NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC00112704

OSTI ID:: 1182536

Report Number(s):: BNL-107637-2015-JA; R&D Project: CO026; KC0304030

Journal Information:: Inorganic Chemistry, Vol. 54, Issue 11; ISSN 0020-1669

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 99 works

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A Precious Catalyst: Rhodium-Catalyzed Formic Acid Dehydrogenation in Water: A Precious Catalyst: Rhodium-Catalyzed Formic Acid Dehydrogenation in Water Fink, Cornel; Laurenczy, Gábor European Journal of Inorganic Chemistry, Vol. 2019, Issue 18 https://doi.org/10.1002/ejic.201900344	journal	April 2019
Enhanced Hydrogen Generation from Formic Acid by Half-Sandwich Iridium(III) Complexes with Metal/NH Bifunctionality: A Pronounced Switch from Transfer Hydrogenation Matsunami, Asuka; Kayaki, Yoshihito; Ikariya, Takao Chemistry - A European Journal, Vol. 21, Issue 39 https://doi.org/10.1002/chem.201502412	journal	August 2015
Half‐sandwich ruthenium complexes with S chiff base ligands bearing a hydroxyl group: Preparation, characterization and catalytic activities Jia, Wei‐Guo; Wang, Zhi‐Bao; Zhi, Xue‐Ting Applied Organometallic Chemistry, Vol. 34, Issue 1 https://doi.org/10.1002/aoc.5289	journal	November 2019
Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water Chakrabarti, Kaushik; Maji, Milan; Kundu, Sabuj Green Chemistry, Vol. 21, Issue 8 https://doi.org/10.1039/c8gc03744b	journal	January 2019
Synthesis of Carboxylic Acids and Esters from CO2 Wu, Xiao-Feng; Zheng, Feng Topics in Current Chemistry, Vol. 375, Issue 1 https://doi.org/10.1007/s41061-016-0091-6	journal	December 2016
Evaluating the impacts of amino acids in the second and outer coordination spheres of Rh-bis(diphosphine) complexes for CO ₂ hydrogenation Walsh, Aaron P.; Laureanti, Joseph A.; Katipamula, Sriram Faraday Discussions, Vol. 215 https://doi.org/10.1039/c8fd00164b	journal	January 2019
Changing the Mechanism for CO ₂ Hydrogenation Using Solvent-Dependent Thermodynamics Burgess, Samantha A.; Appel, Aaron M.; Linehan, John C. Angewandte Chemie International Edition, Vol. 56, Issue 47 https://doi.org/10.1002/anie.201709319	journal	October 2017
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Carbon Nitride as a Ligand: Selective Hydrogenation of Terminal Alkenes Using [(η ⁵ ‐C ₅ Me ₅ )IrCl(g‐C ₃ N ₄ ‐κ ² N,N’ )]Cl Coulson, Ben; Lari, Leonardo; Isaacs, Mark Chemistry – A European Journal https://doi.org/10.1002/chem.201905749	journal	April 2020
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Protic NNN and NCN Pincer-Type Ruthenium Complexes Featuring (Trifluoromethyl)pyrazole Arms: Synthesis and Application to Catalytic Hydrogen Evolution from Formic Acid Nakahara, Yoshiko; Toda, Tatsuro; Matsunami, Asuka Chemistry - An Asian Journal, Vol. 13, Issue 1 https://doi.org/10.1002/asia.201701474	journal	December 2017
Carbon Dioxide Hydrogenation and Formic Acid Dehydrogenation Catalyzed by Iridium Complexes Bearing Pyridyl-pyrazole Ligands: Effect of an Electron-donating Substituent on the Pyrazole Ring on the Catalytic Activity and Durability Onishi, Naoya; Kanega, Ryoichi; Fujita, Etsuko Advanced Synthesis & Catalysis, Vol. 361, Issue 2 https://doi.org/10.1002/adsc.201801323	journal	November 2018
Transfer hydrogenation of carbon dioxide and bicarbonate from glycerol under aqueous conditions Heltzel, Jacob M.; Finn, Matthew; Ainembabazi, Diana Chemical Communications, Vol. 54, Issue 48 https://doi.org/10.1039/c8cc03157f	journal	January 2018
Catalytic reactivity of an iridium complex with a proton responsive N-donor ligand in CO ₂ hydrogenation to formate Gunasekar, Gunniya Hariyanandam; Yoon, Yeahsel; Baek, Il-hyun RSC Advances, Vol. 8, Issue 3 https://doi.org/10.1039/c7ra12343d	journal	January 2018
Iridium–NHC-based catalyst for ambient pressure storage and low temperature release of H ₂ via the CO ₂ /HCO ₂ H couple Semwal, Shrivats; Kumar, Abhishek; Choudhury, Joyanta Catalysis Science & Technology, Vol. 8, Issue 23 https://doi.org/10.1039/c8cy02069h	journal	January 2018
Mixed-valence copper( i,ii ) complexes with 4-(1H-pyrazol-1-yl)-6-R-pyrimidines: from ionic structures to coordination polymers Vinogradova, Katerina A.; Krivopalov, Viktor P.; Nikolaenkova, Elena B. Dalton Transactions, Vol. 45, Issue 2 https://doi.org/10.1039/c5dt04005a	journal	January 2016
Base-free hydrogenation of CO ₂ to formic acid in water with an iridium complex bearing a N,N′-diimine ligand Lu, Sheng-Mei; Wang, Zhijun; Li, Jun Green Chemistry, Vol. 18, Issue 16 https://doi.org/10.1039/c6gc00856a	journal	January 2016
Ruthenium NNN complexes with a 2-hydroxypyridylmethylene fragment for transfer hydrogenation of ketones: Ruthenium complexes for transfer hydrogenation of ketones Shi, Jing; Shang, Shu; Hu, Bowen Applied Organometallic Chemistry, Vol. 32, Issue 2 https://doi.org/10.1002/aoc.4100	journal	October 2017
Iridium Complexes with Proton-Responsive Azole-Type Ligands as Effective Catalysts for CO ₂ Hydrogenation Suna, Yuki; Himeda, Yuichiro; Fujita, Etsuko ChemSusChem, Vol. 10, Issue 22 https://doi.org/10.1002/cssc.201701676	journal	November 2017
Making a Splash in Homogeneous CO ₂ Hydrogenation: Elucidating the Impact of Solvent on Catalytic Mechanisms Wiedner, Eric S.; Linehan, John C. Chemistry – A European Journal, Vol. 24, Issue 64 https://doi.org/10.1002/chem.201801759	journal	July 2018
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Synthesis of Carboxylic Acids and Esters from CO2 Wu, Xiao-Feng; Zheng, Feng Topics in Current Chemistry Collections https://doi.org/10.1007/978-3-319-77757-3_1	book	January 2016
A DFT Study of CO₂Hydrogenation on Faujasite-Supported Ir₄Clusters: on the Role of Water for Selectivity Control Szyja, Bartłomiej M.; Smykowski, Daniel; Szczygieł, Jerzy ChemCatChem, Vol. 8, Issue 15 https://doi.org/10.1002/cctc.201600644	journal	June 2016
Synthesis, Reactivity, and Catalytic Transfer Hydrogenation Activity of Ruthenium Complexes Bearing NNN Tridentate Ligands: Influence of the Secondary Coordination Sphere Shi, Jing; Hu, Bowen; Chen, Xiangyang ACS Omega, Vol. 2, Issue 7 https://doi.org/10.1021/acsomega.7b00410	journal	July 2017

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Title: CO₂ hydrogenation catalyzed by iridium complexes with a proton-responsive ligand