Visible-Light-Induced Organobismuth(III)-Initiated Halogen-Atom Transfer for the Alkylation of Heterocycles with Unactivated Alkyl Iodides
Employing a trace amount of BiPh<sub>3</sub> as a new and sole XAT reagent, a visible-light-induced XAT-enabled protocol for the Minisci alkylation of heterocycles with unactivated iodoalkanes was disclosed. Broad substrate scope and practical applicability were demonstrated by 38 examples with up to 98% yield. Preliminary mechanistic investigations, including DFT calculations, demonstrated a radical pathway. This method features simple operation, no precaution against moisture and oxygen, and EtOH as a green solvent.
Authors
- Gaofeng Feng (ORCID: https://orcid.org/0000-0001-8521-8305)
- Yi-Sha Wang
- Lemao Yu (ORCID: https://orcid.org/0000-0003-3057-274X)
- Tao Cai (ORCID: https://orcid.org/0000-0003-2681-2958)
- Chen Wang (ORCID: https://orcid.org/0000-0003-4736-8251)
- Chao Zhang (ORCID: https://orcid.org/0000-0001-6669-1420)
- Jian Jin (ORCID: https://orcid.org/0000-0001-9685-3355)
- Xuhong Wang (ORCID: https://orcid.org/0009-0009-8371-3180)
Institutions
- Shaoxing University (CN)
- Centre for Alternative Technology (GB)
- Shanghai Institute of Organic Chemistry (CN)
- University of Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-11-03
- DOI
- https://doi.org/10.1021/acs.orglett.5c03755
- Citations
- 4
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.74