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Issue 20, 2012
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o-Benzenedisulfonimide and its chiral derivative as Brønsted acids catalysts for one-pot three-component Strecker reaction. Synthetic and mechanistic aspects

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Abstract

o-Benzenedisulfonimide (OBS) has efficiently catalysed the one-pot three-component reaction of ketones and aromatic amines with trimethylsilyl cyanide (TMSCN) giving the corresponding α-amino nitriles in excellent yields (23 examples; average yield 85%). Reaction conditions were very simple, green and efficient. Theoretical calculations have allowed us to explain the mechanism of this reaction which has been found to take place in two phases; the first consists of the nucleophilic addition of the aniline to the ketone and the subsequent dehydration to an imine; the second one consists of the formal addition of cyanide anion to the protonated imine. OBS acts in all steps of this mechanism. Without an acid catalyst, the reaction mechanism is more simple but barriers are sensibly higher. A chiral derivative of OBS was also used and gave fairly good results.

Graphical abstract: o-Benzenedisulfonimide and its chiral derivative as Brønsted acids catalysts for one-pot three-component Strecker reaction. Synthetic and mechanistic aspects

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Publication details

The article was received on 19 Mar 2012, accepted on 27 Mar 2012 and first published on 27 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB25584G
Org. Biomol. Chem., 2012,10, 4058-4068

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    o-Benzenedisulfonimide and its chiral derivative as Brønsted acids catalysts for one-pot three-component Strecker reaction. Synthetic and mechanistic aspects

    M. Barbero, S. Cadamuro, S. Dughera and G. Ghigo, Org. Biomol. Chem., 2012, 10, 4058
    DOI: 10.1039/C2OB25584G

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