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Selective Reduction of Secondary Amides to Imines Catalysed by Schwartz’s Reagent

Liam Donnelly 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 : The partial reduction of amides is a challenging transformation that must overcome the intrinsic stability of the amide bond and exhibit high chemoselective control to overcome overreduction to amine products. To address this challenge, we describe a zirconium-catalysed synthesis of imines by the reductive deoxygenation of secondary amides. This reaction exploits the excellent chemoselectivity of Schwartz’s reagent (Cp 2 Zr(H)Cl) and utilises (EtO) 3 SiH as a mild stoichiometric reductant to enable catalyst turnover. The reaction generally proceeds with high yields (19 examples, 51 to 95% yield) and tolerates a variety of functional groups (alkene, ester, nitro, etc.). Stoichiometric mechanistic investigations suggest the regeneration of the active [Zr]–H catalyst is achieved through the metathesis of Si–H and Zr–OR σ-bonds.
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Submitted on : Monday, May 23, 2022 - 7:06:15 AM
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Liam Donnelly, Jean-Claude Berthet, Thibault Cantat. Selective Reduction of Secondary Amides to Imines Catalysed by Schwartz’s Reagent. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2022, 61 (33), pp.e202206170. ⟨10.1002/anie.202206170⟩. ⟨cea-03675175⟩



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