Hydride Reduction by a Sodium Hydride-Iodide Composite

Sodium hydride (NaH) is widely used as a Brønsted base in chemical synthesis and reacts with various Brønsted acids, whereas it rarely behaves as a reducing reagent through delivery of the hydride to polar πelectrophiles. This study presents a series of reduction reactions of nitriles, amides, and i...

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Bibliographic Details
Published in:Angewandte Chemie 2016-03, Vol.128 (11), p.3783
Main Authors: Too, Pei Chui, Chan, Guo Hao, Tnay, Ya Lin, Hirao, Hajime, Chiba, Shunsuke
Format: Article
Language:ger
Subjects:
Acids
Amides
Chemical reactions
Chemical synthesis
Chemistry
Cyanides
Imines
Nitriles
Reduction
Sodium
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Summary:Sodium hydride (NaH) is widely used as a Brønsted base in chemical synthesis and reacts with various Brønsted acids, whereas it rarely behaves as a reducing reagent through delivery of the hydride to polar πelectrophiles. This study presents a series of reduction reactions of nitriles, amides, and imines as enabled by NaH in the presence of LiI or NaI. This remarkably simple protocol endows NaH with unprecedented and unique hydride-donor chemical reactivity.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201600305