jo2c00077_si_001.pdf (17.38 MB)
Download file

Synthesis of 5‑Fluoro-dihydroindolizines from Pyrrole-2-acetic Acids and Trifluoromethyl Alkenes via Dual C–F Bond Cleavage in a CF3 Group

Download (17.38 MB)
journal contribution
posted on 17.03.2022, 10:13 authored by Zhengchang Sun, Lei Zhou
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.

History