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Title: 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

Abstract

Cp*Ir (Cp*=pentamethylcyclopentadienyl) complexes with an N,N–bidentate ligand such as 2,2'–bipyridine serve as catalysts for both carbon dioxide (CO2) hydrogenation to formate and formic acid dehydrogenation in water. Previously, it was shown that the introduction of an electron–donating substituent on 2,2'–bipyridine is an effective method to improve the catalytic activity. Especially, the highly electron–donating hydroxyl (OH) substituent performs much better than other substituents such as methyl or methoxy under basic conditions. However, the introduction of an OH substituent on the ligand has been limited to six–membered rings such as pyridine or pyrimidine. These results prompted us to develop a new ligand comprising a pyridyl–pyrazole with an OH group on the pyrazole moiety for Cp*Ir–catalyzed CO2 hydrogenation and formic acid dehydrogenation. In conclusion, the resultant catalyst showed high catalytic activity in CO2 hydrogenation and excellent robustness in formic acid dehydrogenation with a turnover number of 10 million.

Authors:
 [1];  [1]; ORCiD logo [2];  [1]
  1. National Institute of Advanced Industrial Science and Technology, Ibaraki (Japan)
  2. Brookhaven National Lab. (BNL), Upton, NY (United States)
Publication Date:
Research Org.:
Brookhaven National Lab. (BNL), Upton, NY (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1489353
Alternate Identifier(s):
OSTI ID: 1483733
Report Number(s):
BNL-210836-2018-JAAM
Journal ID: ISSN 1615-4150
Grant/Contract Number:  
SC0012704
Resource Type:
Accepted Manuscript
Journal Name:
Advanced Synthesis & Catalysis (ACS)
Additional Journal Information:
Journal Name: Advanced Synthesis & Catalysis (ACS); Journal Volume: 361; Journal Issue: 2; Journal ID: ISSN 1615-4150
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; CO2 hydrogenation; Formic acid dehydrogenation; Iridium catalyst; Hydrogen storage

Citation Formats

Onishi, Naoya, Kanega, Ryoichi, Fujita, Etsuko, and Himeda, Yuichiro. 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. United States: N. p., 2018. Web. doi:10.1002/adsc.201801323.
Onishi, Naoya, Kanega, Ryoichi, Fujita, Etsuko, & Himeda, Yuichiro. 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. United States. doi:10.1002/adsc.201801323.
Onishi, Naoya, Kanega, Ryoichi, Fujita, Etsuko, and Himeda, Yuichiro. Fri . "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". United States. doi:10.1002/adsc.201801323. https://www.osti.gov/servlets/purl/1489353.
@article{osti_1489353,
title = {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},
author = {Onishi, Naoya and Kanega, Ryoichi and Fujita, Etsuko and Himeda, Yuichiro},
abstractNote = {Cp*Ir (Cp*=pentamethylcyclopentadienyl) complexes with an N,N–bidentate ligand such as 2,2'–bipyridine serve as catalysts for both carbon dioxide (CO2) hydrogenation to formate and formic acid dehydrogenation in water. Previously, it was shown that the introduction of an electron–donating substituent on 2,2'–bipyridine is an effective method to improve the catalytic activity. Especially, the highly electron–donating hydroxyl (OH) substituent performs much better than other substituents such as methyl or methoxy under basic conditions. However, the introduction of an OH substituent on the ligand has been limited to six–membered rings such as pyridine or pyrimidine. These results prompted us to develop a new ligand comprising a pyridyl–pyrazole with an OH group on the pyrazole moiety for Cp*Ir–catalyzed CO2 hydrogenation and formic acid dehydrogenation. In conclusion, the resultant catalyst showed high catalytic activity in CO2 hydrogenation and excellent robustness in formic acid dehydrogenation with a turnover number of 10 million.},
doi = {10.1002/adsc.201801323},
journal = {Advanced Synthesis & Catalysis (ACS)},
number = 2,
volume = 361,
place = {United States},
year = {2018},
month = {11}
}

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Cited by: 12 works
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