Lepori, Mattia and Ioannou, Dimitris I. and Barham, Joshua P. and Noël, Timothy (2025) Photocatalyzed hydrogen atom transfer enables multicomponent olefin oxo-amidomethylation under aerobic conditions. CHEMICAL SCIENCE, 16 (48). pp. 22944-22951. ISSN 2041-6520, 2041-6539
Full text not available from this repository. (Request a copy)Abstract
The direct functionalization of abundant and readily available feedstock chemicals has emerged as a powerful strategy to rapidly increase molecular complexity and access valuable scaffolds. Herein, we report a novel photocatalyzed three-component oxo-amidomethylation of aromatic olefins under aerobic conditions, enabling the synthesis of N-(gamma-oxopropyl)amides via simultaneous incorporation of two orthogonal functional groups across the alkene C 00000000 00000000 00000000 00000000 11111111 00000000 11111111 00000000 00000000 00000000 C bond in a single step. Mechanistic features include the photocatalyzed hydrogen atom transfer (HAT)-mediated engagement of the alpha-N-alkyl C(sp3)-H bond in inexpensive, unfunctionalized amide feedstocks and the trapping of a key olefin-derived carbon-centered radical intermediate by molecular oxygen to afford the oxo-functionalized homologated products. This cascade protocol demonstrates compatibility with a broad range of aryl olefins and amides, as well as efficient scalability. The method provides streamlined access to high-value molecular architectures of synthetic and pharmaceutical relevance without the need for pre-functionalized radical precursors.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | OXIDATIVE RADICAL-ADDITION; C(SP(3))-H FUNCTIONALIZATIONS; ASYMMETRIC HYDROGENATION; ORGANIC PEROXIDES; RATE CONSTANTS; KETONES; OXYGEN; ALKYLATION; GENERATION; CHEMISTRY |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 06 May 2026 05:54 |
| Last Modified: | 06 May 2026 05:54 |
| URI: | https://pred.uni-regensburg.de/id/eprint/66864 |
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