Trends in Chemistry
Volume 2, Issue 9, September 2020, Pages 782-784
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A Long-Sought Reactivity of a Sodium Hydride

https://doi.org/10.1016/j.trechm.2020.07.001Get rights and content

Hydride from sodium hydride acts as a base and not as a nucleophile, due to its small size and high charge density. However, recent research has found that a sodium hydride–sodium iodide composite can be a unique hydride donor in the challenging partial reduction of inert amides to imines.

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Acknowledgments

Financial support from the National Science Center, Poland (Grant OPUS 2019/35/B/ST4/02794 for B.F. and Grant PRELUDIUM 2018/29/N/ST5/01938 for P.J.C.) is gratefully acknowledged.

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Cited by (6)

  • Incorporation of germanium into amines via deoxygenative germylation of aromatic amides with hydrogermanes

    2022, Cell Reports Physical Science
    Citation Excerpt :

    Due to the importance of amines in various areas and the significant germanium switch effect,1,2,3 the development of Ge–H insertion reactions of carbenes with N substitutes, preferably generated from simple and widely available precursors, is of considerable interest yet poses a nontrivial challenge for the chemistry community (Figures 1B–1Bii). The natural prevalence and ready synthetic accessibility of amides make them attractive precursors to α-functionalized amines, e.g., via deoxygenative functionalization of the amides.55,56,57,58,59,60,61 However, the inert nature of an amide, as a result of resonance stabilization, generally necessitates the use of harsh conditions and a tedious multi-step process.

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Twitter: @pjczerw (P.J. Czerwiński) and @FurChem (B. Furman).

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