Visible-Light-Induced Nickel-Catalyzed Enantioconvergent C(sp <sup>3</sup> )–C(sp <sup>3</sup> ) Coupling of α-Bromoamides with Alkene-Derived Alkylzirconocenes
) coupling of racemic α-bromoamides with alkylzirconocenes generated in situ from unactivated alkenes is reported. This transformation exploits alkene-derived alkylzirconocenes as redox-active alkyl partners, enabling direct access to enantioenriched α-tertiary aliphatic amides without an external photocatalyst or reductant. Photoinduced C-Zr bond homolysis generates alkyl radicals for capture by a chiral nickel catalyst, while the resulting zirconocene species is proposed to facilitate reductive nickel turnover. The reaction accommodates a range of alkenes and α-bromoamides, delivering the desired products in moderate to good yields and up to 94% ee. The practicality of this method is demonstrated by a scale-up reaction and downstream derivatization of the amide products.
Authors
- Huifeng Yue (ORCID: https://orcid.org/0000-0003-3905-4535)
- Lujie Chen
- Jianguo Han
Institutions
- Chemical Synthesis Lab (SG)
- Fuzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-07-01
- DOI
- https://doi.org/10.1021/acs.orglett.6c02296
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China