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  • Title: Synthesis of 5-Fluoro-dihydroindolizines from Pyrrole-2-acetic Acids and Trifluoromethyl Alkenes via Dual C-F Bond Cleavage in a CF3 Group.
    Author: Sun Z, Zhou L.
    Journal: J Org Chem; 2022 Apr 01; 87(7):4801-4812. PubMed ID: 35297252.
    Abstract:
    Herein, we describe the synthesis of 5-fluoro-dihydroindolizines via dual C-F bond cleavage in a trifluoromethyl group. The photocatalytic defluorinative coupling of pyrrole-2-acetic acids and α-trifluoromethyl alkenes cleaved the first C-F bond, providing gem-difluoroalkenes bearing an unprotected pyrrole motif. Subsequently, an intramolecular SNV reaction closed the ring by forming a C-N bond concomitantly with the cleavage of the second C-F bond. Using indole-2-acetic acids as the substrates, the reactions also allow the assembly of 6-fluoro-dihydropyrido[1,2-a]indoles.
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