Hering, Thea and Meyer, Andreas Uwe and Koenig, Burkhard (2016) Photocatalytic Anion Oxidation and Applications in Organic Synthesis. JOURNAL OF ORGANIC CHEMISTRY, 81 (16). pp. 6927-6936. ISSN 0022-3263,
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Ions and radicals of the same kind differ by one electron only. The oxidation of Many stable inorganic anions yields 3 their corresponding highly reactive radicals, and visible light excitable photocatalysts can provide the required oxidation potential for this transformation. Air oxygen serves as the terminal oxidant, or cheap sacrificial oxidants are used, providing a very practical approach for generating reactive inorganic radicals for organic synthesis. We discuss in this perspective several recently reported examples: Nitrate radicals are obtained by one-electron photooxidation of nitrate anions and are very reactive toward organic Molecules. The photooxidation of sulfinate salts yields the much more stable sulfone radicals, which smoothly add to double bonds. A two-electron oxidation of chloride anions to electrophilic chlorine species reacting with arenes in aromatic substitutions extends the method beyond radical reactions. The chloride anion oxidation proceeds via photocatalytically generated peracidic acid as the oxidation reagent. Although the number of reported examples of photocatalytically generated inorganic radical intermediates for organic synthesis is still small, future extension of the concept to other inorganic ions as radical precursors is a dear perspective.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | VISIBLE-LIGHT; VINYL SULFONES; PHOTOREDOX CATALYSIS; HYDROGEN-PEROXIDE; MECHANISTIC INSIGHT; SODIUM-CHLORIDE; EOSIN Y; ALKENES; NITRATE; CHLORINATION; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 05 Apr 2019 10:57 |
| Last Modified: | 05 Apr 2019 10:57 |
| URI: | https://pred.uni-regensburg.de/id/eprint/3476 |
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