Double addition of organoaluminum reagents onto nitriles to access diethynyl carbinamines

The reactivity of organoaluminum reagents with acyl cyanohydrins was studied using two methods for preparing nucleophilic species. Mild and chemoselective conditions were developed and an unprecedented double addition of dimethylalkynylaluminum reagents onto nitriles provided access to a wide range of substituted diethynyl carbinamines in good to excellent yields (>20 examples).

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob00911a
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
0.00
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article

Double addition of organoaluminum reagents onto nitriles to access diethynyl carbinamines

Fabien Boeda, Giang Nguyen, M. S. M. Pearson-Long, Philippe Bertus
Organic & Biomolecular Chemistry
Chemical Synthesis and Analysis
article

Double addition of organoaluminum reagents onto nitriles to access diethynyl carbinamines

Fabien Boeda, Giang Nguyen, M. S. M. Pearson-Long, Philippe Bertus
article en

Abstract

The reactivity of organoaluminum reagents with acyl cyanohydrins was studied using two methods for preparing nucleophilic species. Mild and chemoselective conditions were developed and an unprecedented double addition of dimethylalkynylaluminum reagents onto nitriles provided access to a wide range of substituted diethynyl carbinamines in good to excellent yields (>20 examples).

Organic & Biomolecular ChemistryVol. 23(34)
Centre National de la Recherche Scientifique (FR), Institut des Molécules et Matériaux du Mans (FR)
Openalex Percentile: Top 84%
Chemical Synthesis and Analysis
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