Ganie, Majid Ahmad and Roy, Niladri Sekhar and Raza, Arslan and Koenig, Burkhard and Sarkar, Debayan (2025) Flavin-Photocatalyzed Benzylic Functionalization, Spirocyclization, and Spiroepoxidation of Phenols. ACS CATALYSIS, 15 (20). pp. 17078-17088. ISSN 2155-5435
Full text not available from this repository. (Request a copy)Abstract
para-Quinone methides (p-QMs) are versatile, transient electrophilic dearomatized intermediates in organic synthesis, enabling a range of transformations, such as cycloadditions, nucleophilic additions, and cascade reactions. Conventionally, these ephemeral species are generated in situ via acid- or base-mediated activation of phenols prefunctionalized with a leaving group (e.g., hydroxyl, halide, or sulfonate) at the benzylic position or through oxidation of phenols employing toxic heavy metal salts (e.g., lead, silver, or bismuth). We report a photocatalytic approach for in situ generation of p-QMs directly from simple phenolic precursors, thereby circumventing the need for benzylic prefunctionalization or transition-metal reagents. The photogenerated p-QMs undergo efficient transformations, including benzylic functionalization, spirocyclization, and spiroepoxidation, delivering rapid access to benzylic scaffolds and structurally complex sp3-rich spirocyclic frameworks. The synthetic utility of this approach is further demonstrated by the late-stage functionalization of drugs and natural products.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PARA-QUINONE METHIDES; BIOMIMETIC SYNTHESES; ELECTRON-TRANSFER; SINGLET OXYGEN; VISIBLE-LIGHT; DEAROMATIZATION; POLYDOPAMINE; GENERATION; REACTIVITY; EUMELANIN; <italic>para</italic>-quinone methides; dearomatization; benzylic functionalization; spirocyclization; spiroepoxidation |
| 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: | 13 Aug 2026 04:33 |
| Last Modified: | 13 Aug 2026 04:33 |
| URI: | https://pred.uni-regensburg.de/id/eprint/66489 |
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