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DOI: 10.1055/sos-SD-225-00172

Chemler, S. R.; Wdowik, T.Science of Synthesis: Catalytic Oxidation in Organic Synthesis, (20171385.

Formation of oxygen heterocycles 89 via alkene aminooxygenation of unsaturated hydroxamic acids 88 is possible using a metal-free approach (Table 11). The reaction involves an amidoxyl radical and leads to the construction of five- and six-membered rings. The reaction of cyclic alkenes provides trans-aminooxygenation products (entries 4 and 5).[‌80‌] Aminooxygenation proceeds without any additional reagents other than an alkene (with a tethered oxygen source) and a nitrogen source (diisopropyl azodicarboxylate). A radical mechanism is proposed where the reaction is initiated by a small amount of an amidoxyl radical formed by autoxidation.

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