Straightforward access to cyclic amines by dinitriles reduction

Abstract : 1,1,3,3-Tetramethyldisiloxane (TMDS) and polymethylhydrosiloxane (PMHS), when associated with titanium(IV) isopropoxide, provide two convenient systems for the reduction of nitriles into the corresponding primary amines. Kinetics of the two systems have been studied by 1H NMR and demonstrated that reduction with PMHS occurs faster than with TMDS. These two titanium-based systems reduce both aromatic and aliphatic nitriles in the presence of Br, Cdouble bond; length as m-dashC, NO2, OH, and cyclopropyl-ring. In the case of cyclopropyl-nitriles, the formation of secondary amines, which come from an intermolecular reductive alkylation reaction was observed. This result was exploited for the reduction of dinitriles, which led, in one-step, to azepane, piperidine, pyrrolidine, and azetidine derivatives through an intramolecular reductive alkylation reaction.
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Submitted on : Wednesday, July 22, 2015 - 4:25:50 PM
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  • HAL Id : hal-01179511, version 1


Stéphane Laval, Wissam Dayoub, Leyla Pehlivan, Estelle Métay, Alain Favre-Reguillon, et al.. Straightforward access to cyclic amines by dinitriles reduction. Tetrahedron, Elsevier, 2014, 70 (4), pp.975-983. ⟨hal-01179511⟩



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