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Revision as of 22:30, 24 December 2024 by DMacks (talk | contribs) (new thing)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)Ammonium hypoiodites are a class of reactive intermediates used in certain organic oxidation reactions. They consist of either ammonium itself or a alkylammonium with various substituents as cation, paired with an hypoiodite anion as the active oxidant. The hypoiodite is generated in situ from the analogous iodide reagent using peroxides, oxone, peracids, or other strong oxidizing agents. The hypoiodite is then capable of oxidizing benzylic methyl groups, initiating oxidative dearomatization, and oxidative decarboxylation of β-ketolactones. The iodide is regenerated, meaning the reaction runs with the iodide/hypoiodite as a catalyst in the presence of excess of the other oxidizing agent.
References
- Yusubov, Mekhman S.; Zhdankin, Viktor V. (2015). "Iodine catalysis: A green alternative to transition metals in organic chemistry and technology". Resource-Efficient Technologies. 1 (1): 49–67. Bibcode:2015RETec...1...49Y. doi:10.1016/j.reffit.2015.06.001.
- Pollheimer, David; Mairhofer, Christopher; Waser, Mario (2024). "Syntheses of Diarylmethanes Via an Oxidative Benzylic Functionalization of P-Alkyl Phenol Derivatives Under Quaternary Ammonium Hypoiodite Catalysis". Chemistry – A European Journal. 30 (54): e202402528. doi:10.1002/chem.202402528. PMID 39054252.
- Uyanik, Muhammet; Kato, Takehiro; Sahara, Naoto; Katade, Outa; Ishihara, Kazuaki (2019). "High-Performance Ammonium Hypoiodite/Oxone Catalysis for Enantioselective Oxidative Dearomatization of Arenols". ACS Catalysis. 9 (12): 11619–11626. doi:10.1021/acscatal.9b04322.
- Röser, Katharina; Scheucher, Anna; Mairhofer, Christopher; Bechmann, Matthias; Waser, Mario (2022). "Oxidative decarboxylative ammonium hypoiodite-catalysed dihydrobenzofuran synthesis". Organic & Biomolecular Chemistry. 20 (16): 3273–3276. doi:10.1039/D2OB00463A. PMID 35363244.
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