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Kang, H. Diimide Reduction. Encyclopedia. Available online: https://encyclopedia.pub/entry/60318 (accessed on 03 October 2026).
Kang H. Diimide Reduction. Encyclopedia. Available at: https://encyclopedia.pub/entry/60318. Accessed October 03, 2026.
Kang, Helena. "Diimide Reduction" Encyclopedia, https://encyclopedia.pub/entry/60318 (accessed October 03, 2026).
Kang, H. (2026, September 23). Diimide Reduction. In Encyclopedia. https://encyclopedia.pub/entry/60318
Kang, Helena. "Diimide Reduction." Encyclopedia. Web. 23 September, 2026.
Diimide Reduction
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Transfer of hydrogen from diimide (HN=NH) to a carbon–carbon multiple bond constitutes diimide reduction. The reagent is generated in situ, typically by oxidation of hydrazine or by thermal decomposition of an arylsulfonylhydrazide, and delivers both hydrogen atoms in a concerted, syn fashion to an alkene or alkyne through a six-membered transition state. Carbonyl groups, nitro groups, and most aromatic rings are not reduced under standard conditions, so the process is a chemoselective saturation of C=C and C≡C bonds rather than a general hydride reduction of carbonyls to alcohols. The method applies to solution-phase and solid-supported alkenes [1]. Organocatalytic generation of diimide enables reduction of enamides in water while preserving the same HN=NH delivery step [2]. Selective diimide reduction has been used to saturate a strained alkene in the presence of a peroxide, underscoring discrimination between a C=C bond and other reducible functions [3]. The concept is bounded as stoichiometric or catalytic use of diimide as the hydrogen donor, distinct from catalytic hydrogenation on a metal surface and from dissolving-metal reduction.

diimide reduction HN=NH syn hydrogenation selective alkene reduction

References

  1. Keith R. Buszek; Neil Brown; Improved Method for the Diimide Reduction of Multiple Bonds on Solid-Supported Substrates. J. Org. Chem. 2007, 72, 3125-3128. [CrossRef]
  2. Barrie J. Marsh; Emma L. Heath; David R. Carbery; Organocatalytic diimide reduction of enamides in water. Chem. Commun. 2010, 47, 280-282. [CrossRef]
  3. Waldemar Adam; Henny J. Eggelte; Prostanoid endoperoxide model compounds: 2,3-dioxabicyclo[2.2.1]heptane via selective diimide reduction. J. Org. Chem. 1977, 42, 3987-3988. [CrossRef]
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Subjects: Chemistry, Organic
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Update Date: 23 Sep 2026
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