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Uranyl(VI) Triflate as Catalyst for the Meerwein–Ponndorf–Verley Reaction

Marie Kobylarski 1 Louis Monsigny 1 Pierre Thuéry 1 Jean-Claude Berthet 1 Thibault Cantat 1 
1 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)
NIMBE UMR 3685 - Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M)
Abstract : Catalytic transformation of oxygenated compounds is challenging in f-element chemistry due to the high oxophilicity of the f-block metals. We report here the first Meerwein–Ponndorf–Verley (MPV) reduction of carbonyl substrates with uranium-based catalysts, in particular from a series of uranyl(VI) compounds where [UO2(OTf)2] (1) displays the greatest efficiency (OTf = trifluoromethanesulfonate). [UO2(OTf)2] reduces a series of aromatic and aliphatic aldehydes and ketones into their corresponding alcohols with moderate to excellent yields, using iPrOH as a solvent and a reductant. The reaction proceeds under mild conditions (80 °C) with an optimized catalytic charge of 2.3 mol % and KOiPr as a cocatalyst. The reduction of aldehydes (1–10 h) is faster than that of ketones (>15 h). NMR investigations clearly evidence the formation of hemiacetal intermediates with aldehydes, while they are not formed with ketones.
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Submitted on : Tuesday, October 19, 2021 - 7:28:49 AM
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Marie Kobylarski, Louis Monsigny, Pierre Thuéry, Jean-Claude Berthet, Thibault Cantat. Uranyl(VI) Triflate as Catalyst for the Meerwein–Ponndorf–Verley Reaction. Inorganic Chemistry, American Chemical Society, In press, 60, pp.16140-16148. ⟨10.1021/acs.inorgchem.1c01798⟩. ⟨cea-03384490⟩



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