Dual Photoexcited Palladium and Photoredox-Catalyzed Remote C(sp<sup>3</sup>)–H Acylation of Hydroxyamides
Herein, we report an unprecedented dual photoexcited palladium and photoredox-catalyzed remote C(sp<sup>3</sup>)-H acylation of amides free of external acylating reagents through sequential N-O/C-H/C-O bond cleavage and chemoselective C-C bond formation. This dual catalytic system shows high efficiency, good atom economy by deletion of oxygen, and diverse functional group tolerance. Experimental investigation of the reaction mechanism revealed that <i>O</i>-acyl hydroxamides enabled by photoexcited palladium generated the alkyl radicals via a 1,5-HAT process mediated by amidyl radicals and a palladium carboxylate complex, which, undergoing photoredox-catalyzed phosphoranyl radical-mediated C-O bond cleavage, leads to coupling with alkyl radicals to deliver the final products.
Authors
- Jun Wang (ORCID: https://orcid.org/0000-0002-4035-2786)
- Siping Wei (ORCID: https://orcid.org/0000-0002-1084-8772)
- Daling Li
- Qiang Fu (ORCID: https://orcid.org/0000-0001-9993-8776)
- Lingmin Zhou
- Xianchao Pan (ORCID: https://orcid.org/0000-0002-1269-683X)
- Lin Yang (ORCID: https://orcid.org/0000-0003-2191-9027)
- Yingfeng Yu (ORCID: https://orcid.org/0000-0002-2607-0416)
- Lixu Ren
- Jun Wei (ORCID: https://orcid.org/0000-0001-6002-3413)
- Ji Lu (ORCID: https://orcid.org/0000-0001-8225-4140)
- Na Hao (ORCID: https://orcid.org/0000-0002-4527-8167)
- Liya Huang
Institutions
- Southwest Medical University (CN)
- Green Chemistry (PL)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-21
- DOI
- https://doi.org/10.1021/acs.orglett.5c00881
- Citations
- 4
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- National Natural Science Foundation of China
- Department of Science and Technology of Sichuan Province
- Luzhou Science and Technology Bureau