Iridium-Catalyzed Transfer Hydrogenation of Ketones and Aldehydes Using Glucose as a Sustainable Hydrogen Donor

A new catalytic system for transfer hydrogenation of carbonyl compounds using glucose as a hydrogen donor was developed. Various ketones and aldehydes were efficiently converted to corresponding alcohols with two equivalents of glucose in the presence of a small amount (0.1 to 1.0 mol%) of iridium c...

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Main Authors: Masato Yoshida, Ryota Hirahata, Takayoshi Inoue, Takuya Shimbayashi, Ken-ichi Fujita
Format: Article
Language:English
Published: MDPI AG 2019-05-01
Series:Catalysts
Subjects:
Online Access:https://www.mdpi.com/2073-4344/9/6/503
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author Masato Yoshida
Ryota Hirahata
Takayoshi Inoue
Takuya Shimbayashi
Ken-ichi Fujita
author_facet Masato Yoshida
Ryota Hirahata
Takayoshi Inoue
Takuya Shimbayashi
Ken-ichi Fujita
author_sort Masato Yoshida
collection DOAJ
description A new catalytic system for transfer hydrogenation of carbonyl compounds using glucose as a hydrogen donor was developed. Various ketones and aldehydes were efficiently converted to corresponding alcohols with two equivalents of glucose in the presence of a small amount (0.1 to 1.0 mol%) of iridium catalyst that had a functional ligand. In this catalytic system, transfer hydrogenation reactions proceeded based on the cooperativity of iridium and a functional ligand. It should be noted that environmentally benign water could have been used as a solvent in the present catalytic system for the reduction of various carbonyl substrates. Furthermore, the reaction scope could be extended by using <i>N,N</i>-dimethylacetamide as a reaction solvent.
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spelling doaj.art-753590175047431386e1ba0cf6d1a00c2022-12-22T03:17:55ZengMDPI AGCatalysts2073-43442019-05-019650310.3390/catal9060503catal9060503Iridium-Catalyzed Transfer Hydrogenation of Ketones and Aldehydes Using Glucose as a Sustainable Hydrogen DonorMasato Yoshida0Ryota Hirahata1Takayoshi Inoue2Takuya Shimbayashi3Ken-ichi Fujita4Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, JapanGraduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, JapanGraduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, JapanGraduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, JapanGraduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, JapanA new catalytic system for transfer hydrogenation of carbonyl compounds using glucose as a hydrogen donor was developed. Various ketones and aldehydes were efficiently converted to corresponding alcohols with two equivalents of glucose in the presence of a small amount (0.1 to 1.0 mol%) of iridium catalyst that had a functional ligand. In this catalytic system, transfer hydrogenation reactions proceeded based on the cooperativity of iridium and a functional ligand. It should be noted that environmentally benign water could have been used as a solvent in the present catalytic system for the reduction of various carbonyl substrates. Furthermore, the reaction scope could be extended by using <i>N,N</i>-dimethylacetamide as a reaction solvent.https://www.mdpi.com/2073-4344/9/6/503transfer hydrogenationiridium catalystfunctional ligandglucoseketonealdehydealcoholwater solvent
spellingShingle Masato Yoshida
Ryota Hirahata
Takayoshi Inoue
Takuya Shimbayashi
Ken-ichi Fujita
Iridium-Catalyzed Transfer Hydrogenation of Ketones and Aldehydes Using Glucose as a Sustainable Hydrogen Donor
Catalysts
transfer hydrogenation
iridium catalyst
functional ligand
glucose
ketone
aldehyde
alcohol
water solvent
title Iridium-Catalyzed Transfer Hydrogenation of Ketones and Aldehydes Using Glucose as a Sustainable Hydrogen Donor
title_full Iridium-Catalyzed Transfer Hydrogenation of Ketones and Aldehydes Using Glucose as a Sustainable Hydrogen Donor
title_fullStr Iridium-Catalyzed Transfer Hydrogenation of Ketones and Aldehydes Using Glucose as a Sustainable Hydrogen Donor
title_full_unstemmed Iridium-Catalyzed Transfer Hydrogenation of Ketones and Aldehydes Using Glucose as a Sustainable Hydrogen Donor
title_short Iridium-Catalyzed Transfer Hydrogenation of Ketones and Aldehydes Using Glucose as a Sustainable Hydrogen Donor
title_sort iridium catalyzed transfer hydrogenation of ketones and aldehydes using glucose as a sustainable hydrogen donor
topic transfer hydrogenation
iridium catalyst
functional ligand
glucose
ketone
aldehyde
alcohol
water solvent
url https://www.mdpi.com/2073-4344/9/6/503
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AT ryotahirahata iridiumcatalyzedtransferhydrogenationofketonesandaldehydesusingglucoseasasustainablehydrogendonor
AT takayoshiinoue iridiumcatalyzedtransferhydrogenationofketonesandaldehydesusingglucoseasasustainablehydrogendonor
AT takuyashimbayashi iridiumcatalyzedtransferhydrogenationofketonesandaldehydesusingglucoseasasustainablehydrogendonor
AT kenichifujita iridiumcatalyzedtransferhydrogenationofketonesandaldehydesusingglucoseasasustainablehydrogendonor