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Product-Catalyzed Addition of Alkyl Nitriles to Unactivated Imines Promoted by Sodium Aryloxide/Ethyl(trimethylsilyl)acetate (ETSA) Combination

Thomas Poisson 1 Vincent Gembus 1 Sylvain Oudeyer 1 Francis Marsais 1 Vincent Levacher 1
1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
Abstract : The first transition-metal-free addition of alkyl nitriles to unactivated imines was developed using a catalytic combination of 4-MeOC6H4ONa and TMSCH2CO2Et to promote the reaction. The corresponding β-amino nitriles are obtained in good to almost quantitative isolated yields under mild conditions. A mechanism involving an autocatalytic pathway is proposed on the basis of experimental observations.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02278746
Contributor : Sylvain Oudeyer <>
Submitted on : Wednesday, September 4, 2019 - 3:39:15 PM
Last modification on : Thursday, July 2, 2020 - 3:28:44 AM

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COMUE-NORMANDIE | CNRS | INC-CNRS | INSA-ROUEN | UNIROUEN | COBRA | INSA-GROUPE | ENSICAEN | UNILEHAVRE | UNICAEN

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Thomas Poisson, Vincent Gembus, Sylvain Oudeyer, Francis Marsais, Vincent Levacher. Product-Catalyzed Addition of Alkyl Nitriles to Unactivated Imines Promoted by Sodium Aryloxide/Ethyl(trimethylsilyl)acetate (ETSA) Combination. Journal of Organic Chemistry, American Chemical Society, 2009, 74 (9), pp.3516-3519. ⟨10.1021/jo802763b⟩. ⟨hal-02278746⟩

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