Photoredox-Catalyzed Cascade Difluoroalkylation and Intramolecular Cyclization for Construction of Fluorinated γ‑Butyrolactones

A cascade visible-light photocatalytic difluoroalkylation and intramolecular cyclization reaction has been developed for the synthesis of difluoroalkylated oxygen heterocycles. The reaction was carried out under very mild conditions, affording fluorinated isobenzofuran-1-ones, lactone, and cyclic et...

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Veröffentlicht in:Journal of organic chemistry 2017-09, Vol.82 (18), p.9824-9831
Hauptverfasser: Sha, Wanxing, Zhang, Wenzhong, Ni, Shengyang, Mei, Haibo, Han, Jianlin, Pan, Yi
Format: Artikel
Sprache:eng
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Zusammenfassung:A cascade visible-light photocatalytic difluoroalkylation and intramolecular cyclization reaction has been developed for the synthesis of difluoroalkylated oxygen heterocycles. The reaction was carried out under very mild conditions, affording fluorinated isobenzofuran-1-ones, lactone, and cyclic ethers with up to 97% chemical yields. Furthermore, several types of bromofluoroalkane precursors bearing ester, keto, amido, and phosphate groups could all work very well in this reaction, which provides an easy method for the preparation of functionalized difluoroalkylated oxygen heterocycles.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b01279