Hydride Reduction by a Sodium Hydride-Iodide Composite

Pei Chui Too; Guo Hao Chan; Ya Lin Tnay; Hajime Hirao; Shunsuke Chiba

doi:10.1002/anie.201600305

Hydride Reduction by a Sodium Hydride-Iodide Composite

Pei Chui Too, Guo Hao Chan, Ya Lin Tnay, Hajime Hirao, Shunsuke Chiba

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

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Abstract

Sodium hydride (NaH) is widely used as a BrÃ¸nsted base in chemical synthesis and reacts with various BrÃ¸nsted 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.

Original language	English
Pages (from-to)	3719-3723
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	11
DOIs	https://doi.org/10.1002/anie.201600305
Publication status	Published - 7 Mar 2016
Externally published	Yes

Research Keywords

amides
decyanation
density functional calculations
reduction
sodium hydride

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This full text is made available under CC-BY-NC 4.0. https://creativecommons.org/licenses/by-nc/4.0/

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AU - Chiba, Shunsuke

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N2 - Sodium hydride (NaH) is widely used as a BrÃ¸nsted base in chemical synthesis and reacts with various BrÃ¸nsted 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.

AB - Sodium hydride (NaH) is widely used as a BrÃ¸nsted base in chemical synthesis and reacts with various BrÃ¸nsted 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.

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KW - density functional calculations

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M3 - RGC 21 - Publication in refereed journal

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JO - Angewandte Chemie - International Edition

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Hydride Reduction by a Sodium Hydride-Iodide Composite

Abstract

Research Keywords

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