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Hydride Reduction by a Sodium Hydride-Iodide Composite.


ABSTRACT: 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 ??electrophiles. 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.

SUBMITTER: Too PC 

PROVIDER: S-EPMC4797714 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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Hydride Reduction by a Sodium Hydride-Iodide Composite.

Too Pei Chui PC   Chan Guo Hao GH   Tnay Ya Lin YL   Hirao Hajime H   Chiba Shunsuke S  

Angewandte Chemie (International ed. in English) 20160216 11


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 π electrophiles. 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. ...[more]

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