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Open AccessArticle

Effect of a Substituent in Cyclopentadienyl Ligand on Iridium-Catalyzed Acceptorless Dehydrogenation of Alcohols and 2-Methyl-1,2,3,4-tetrahydroquinoline

Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan
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Author to whom correspondence should be addressed.
Catalysts 2019, 9(10), 846; https://doi.org/10.3390/catal9100846
Received: 24 September 2019 / Revised: 2 October 2019 / Accepted: 3 October 2019 / Published: 12 October 2019
(This article belongs to the Special Issue Transition-Metal-Catalyzed Reactions in Organic Synthesis)
New iridium(III)-bipyridonate complexes having cyclopentadienyl ligands with a series of alkyl substituents were synthesized for the purpose of tuning the catalytic activity for acceptorless dehydrogenation reactions. A comparison of the catalytic activity was performed for the reaction of alcoholic substrates such as 1-phenylethanol, 2-octanol, and benzyl alcohol. The 1-t-butyl-2,3,4,5-tetramethylcyclopentadienyl iridium complex exhibited the best performance, which surpassed that of the 1,2,3,4,5-pentamethylcyclopentadienyl (Cp*) iridium catalyst in the dehydrogenation reaction of alcohols. The catalytic activity in the dehydrogenation of 2-methyl-1,2,3,4-tetrahydroquinoline was also examined. The highest efficiency was obtained in the reaction catalyzed by the same t-butyl-substituted cyclopentadienyl iridium complex. View Full-Text
Keywords: iridium complex; cyclopentadienyl ligand; functional ligand; catalytic dehydrogenation; alcohol; N-heterocycle iridium complex; cyclopentadienyl ligand; functional ligand; catalytic dehydrogenation; alcohol; N-heterocycle
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MDPI and ACS Style

Jeong, J.; Shimbayashi, T.; Fujita, K.-I. Effect of a Substituent in Cyclopentadienyl Ligand on Iridium-Catalyzed Acceptorless Dehydrogenation of Alcohols and 2-Methyl-1,2,3,4-tetrahydroquinoline. Catalysts 2019, 9, 846.

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