Organophotoredox-Catalyzed Fluoroalkylation of Morita–Baylis–Hillman Adducts Using Quaternary Fluoroalkyl Alcohols as the Fluoroalkylating Reagents
Photoredox-enabled fluoroalkylation of MBH adducts using quaternary fluoroalkyl alcohols as the fluoroalkylating radical reagents is described. The facile protocol displays excellent functional group tolerance toward a series of synthetic allyl scaffolds containing fluoroalkyl groups under mild conditions. The alternative wavelength of visible light delivers the desired product with different yields and <i>Z/E</i> selectivities. A radical pathway involving an O-centered radical that induces β-scission to form the key fluoroalkyl radical is proposed in this transformation.
Authors
- Qiang Zhao (ORCID: https://orcid.org/0000-0003-2705-5004)
- Xianchao Du (ORCID: https://orcid.org/0009-0002-8284-5834)
- Wenchao Gao (ORCID: https://orcid.org/0000-0002-6106-6287)
- Cun‐Duo Tang (ORCID: https://orcid.org/0000-0003-0352-0805)
- Ting Li (ORCID: https://orcid.org/0000-0002-2186-6992)
- Wenguang Li (ORCID: https://orcid.org/0009-0003-4969-4621)
- Yong Teng
- Xin Li (ORCID: https://orcid.org/0009-0003-7880-296X)
Institutions
- Institute of Catalysis and Petrochemistry (RU)
- Nanyang Normal University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-10-15
- DOI
- https://doi.org/10.1021/acs.joc.5c01991
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00