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Issue 91, 2016
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Aqueous biphasic iron-catalyzed asymmetric transfer hydrogenation of aromatic ketones

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Abstract

For the first time, an iron(II) catalyst is used in the biphasic asymmetric transfer hydrogenation (ATH) of ketones to enantioenriched alcohols employing water and potassium formate as the proton and hydride source, respectively. The precatalyst [FeCl(CO)(P–NH–N–P)]BF4 (P–NH–N–P = (S,S)-PPh2CH2CH2NHCHPhCHPhNCHCH2PPh2) in the organic phase with the substrate is activated by base to produce a system that rivals the best ruthenium biphasic ATH catalysts in activity but not enantioselectivity. Biorenewable 2-methyltetrahydrofuran as a cosolvent and biodegradable TWEEN80 as a surfactant were added to the reaction mixture to greatly decrease the mass-transfer limitations caused by the biphasic reaction mixture. The enantioselectivity of the reduction was as high as 76% depending on the substitution pattern of the arylketone employed. NMR studies verified the formation of an iron hydride [FeH(CO)(PPh2CH2CH2NHCHPhCHPhNCHCHPPh2)] intermediate as was observed in our 2-propanol-based ATH studies.

Graphical abstract: Aqueous biphasic iron-catalyzed asymmetric transfer hydrogenation of aromatic ketones

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Publication details

The article was received on 08 Sep 2016, accepted on 09 Sep 2016 and first published on 09 Sep 2016


Article type: Paper
DOI: 10.1039/C6RA22538A
Citation: RSC Adv., 2016,6, 88580-88587
  • Open access: Creative Commons BY license
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    Aqueous biphasic iron-catalyzed asymmetric transfer hydrogenation of aromatic ketones

    K. Z. Demmans, O. W. K. Ko and R. H. Morris, RSC Adv., 2016, 6, 88580
    DOI: 10.1039/C6RA22538A

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