Three-Component Photocatalyzed Difunctionalization of Alkenes via Selective Remote 1,5-HAT of <i>N</i>-Alkoxyphthalimides and a Radical-Polar Crossover Process
Photocatalyzed difunctionalization of alkenes via radical-polar crossover (RPC) has been significantly advanced. <i>N</i>-Alkoxyphthalimides (NHPIs) have served as alkoxy radical precursors for alcohol synthesis. We report the first metal catalyst-free, three-component difunctionalization of alkenes employing NHPIs through selective remote 1,5-hydrogen atom transfer (HAT) and RPC. This protocol accommodates a broad substrate scope, affording products in moderate to good yields. Mechanistic studies (control reactions, radical/cation trapping, Stern-Volmer quenching, and cyclic voltammetry) elucidate the reaction pathway.
Authors
- Tianle Huang (ORCID: https://orcid.org/0009-0009-0184-7899)
- Qing Liu (ORCID: https://orcid.org/0000-0001-9402-0595)
- Zhongzhen Yang (ORCID: https://orcid.org/0000-0002-3963-3847)
- Yong Wu (ORCID: https://orcid.org/0000-0003-0719-4963)
- Hai Li (ORCID: https://orcid.org/0000-0002-9659-1153)
- Yafei Zhu (ORCID: https://orcid.org/0009-0000-1002-0708)
Institutions
- Sichuan University (CN)
- West China Hospital of Sichuan University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-08-04
- DOI
- https://doi.org/10.1021/acs.orglett.5c02827
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00