Product-Catalyzed Addition of Alkyl Nitriles to Unactivated Imines Promoted by Sodium Aryloxide/Ethyl(trimethylsilyl)acetate (ETSA) Combination - Normandie Université Access content directly
Journal Articles Journal of Organic Chemistry Year : 2009

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

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.
No file

Dates and versions

hal-02278746 , version 1 (04-09-2019)

Identifiers

Cite

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, 2009, 74 (9), pp.3516-3519. ⟨10.1021/jo802763b⟩. ⟨hal-02278746⟩
21 View
0 Download

Altmetric

Share

Gmail Facebook X LinkedIn More