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Iron-catalyzed hydrosilylation of diacids in the presence of amines: a new route to cyclic amines

Abstract : Cyclic amines (such as pyrrolidines, piperidines and azepanes) are present in a large class of natural products and bioactive molecules. Herein, we present a novel chemoselective strategy for buildingN-substituted cyclic aminesviairon catalyzed one-pot hydrosilylation starting from readily available dicarboxylic acids and amines, with hydrosilanes as the hydride sources. The described methodology allows the preparation of a wide range ofN-alkylated and arylated cyclic amine derivatives (including pharmaceuticals Fenpiprane and Prozapine) in moderate to excellent yields, starting from inexpensive succinic, glutaric, and adipic acids with dimethyl carbonate as a green solvent.
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Submitted on : Thursday, October 8, 2020 - 3:19:04 PM
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Duo Wei, Chakkrit Netkaew, J Wu, Christophe Darcel. Iron-catalyzed hydrosilylation of diacids in the presence of amines: a new route to cyclic amines. ChemCatChem, Wiley, 2020, 12 (21), pp.5449-5455. ⟨10.1002/cctc.202000881⟩. ⟨hal-02957751⟩

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