Stable and reactive diacetyliminoxyl radical in oxidative C–O coupling with β-dicarbonyl compounds and their complexes. Issue 35 (25th August 2021)

• Record Type: Journal Article
• Authors: Budnikov, Alexander S.; Krylov, Igor B.; Lastovko, Andrey V.; Paveliev, Stanislav A.; Romanenko, Alexander R.; Nikishin, Gennady I.; Terent'ev, Alexander O.
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 35(2021)
• Page Start: 7581
• Page End: 7586
• Publication Date: 2021-08-25
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01269j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Between oxime radicals, which were generally considered as unstable intermediates, one of the simplest was found to be a storable, synthetically available, and useful reagent. Abstract : As a rule, reactive free radicals used in organic synthesis are too labile to be isolated, whereas persistent radicals are inert and find limited synthetic application. In the present study, the unusually stable diacetyliminoxyl radical was presented as a "golden mean" between transient and stable unreactive radicals. It was successfully employed as a reagent for oxidative C–O coupling with β-dicarbonyl compounds. Using this model radical the catalytic activity of acids, bases and transition metal ions in free-radical coupling was revealed.