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 π electrophiles. This study presents a series of reduction reactions of nitriles, amides, and...

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Detalles Bibliográficos
Autores principales: Too, Pei Chui, Chan, Guo Hao, Tnay, Ya Lin, Hirao, Hajime, Chiba, Shunsuke
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4797714/
https://www.ncbi.nlm.nih.gov/pubmed/26878823
http://dx.doi.org/10.1002/anie.201600305
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author Too, Pei Chui
Chan, Guo Hao
Tnay, Ya Lin
Hirao, Hajime
Chiba, Shunsuke
author_facet Too, Pei Chui
Chan, Guo Hao
Tnay, Ya Lin
Hirao, Hajime
Chiba, Shunsuke
author_sort Too, Pei Chui
collection PubMed
description 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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spelling pubmed-47977142016-03-21 Hydride Reduction by a Sodium Hydride–Iodide Composite Too, Pei Chui Chan, Guo Hao Tnay, Ya Lin Hirao, Hajime Chiba, Shunsuke Angew Chem Int Ed Engl Communications 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. John Wiley and Sons Inc. 2016-02-16 2016-03-07 /pmc/articles/PMC4797714/ /pubmed/26878823 http://dx.doi.org/10.1002/anie.201600305 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Too, Pei Chui
Chan, Guo Hao
Tnay, Ya Lin
Hirao, Hajime
Chiba, Shunsuke
Hydride Reduction by a Sodium Hydride–Iodide Composite
title Hydride Reduction by a Sodium Hydride–Iodide Composite
title_full Hydride Reduction by a Sodium Hydride–Iodide Composite
title_fullStr Hydride Reduction by a Sodium Hydride–Iodide Composite
title_full_unstemmed Hydride Reduction by a Sodium Hydride–Iodide Composite
title_short Hydride Reduction by a Sodium Hydride–Iodide Composite
title_sort hydride reduction by a sodium hydride–iodide composite
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4797714/
https://www.ncbi.nlm.nih.gov/pubmed/26878823
http://dx.doi.org/10.1002/anie.201600305
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AT changuohao hydridereductionbyasodiumhydrideiodidecomposite
AT tnayyalin hydridereductionbyasodiumhydrideiodidecomposite
AT hiraohajime hydridereductionbyasodiumhydrideiodidecomposite
AT chibashunsuke hydridereductionbyasodiumhydrideiodidecomposite

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