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

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

76 Citations (Scopus)

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 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
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	11
DOIs	https://doi.org/10.1002/anie.201600305
Publication status	Published - Mar 7 2016
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

amides
decyanation
density functional calculations
reduction
sodium hydride

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10.1002/anie.201600305

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abstract = "Sodium hydride (NaH) is widely used as a Br{\o}nsted base in chemical synthesis and reacts with various Br{\o}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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AU - Hirao, Hajime

AU - Chiba, Shunsuke

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N2 - 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.

AB - 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.

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KW - density functional calculations

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Hydride Reduction by a Sodium Hydride-Iodide Composite

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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