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Phototriggered Fluoroalkylation/Cyclization of Unactivated 1‑Acryloyl-2-cyanoindoles: Synthesis of RCOCF2‑Substituted Pyrrolo[1,2‑a]indolediones

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posted on 2024-02-16, 10:34 authored by Weixian Lv, Pengyuan Yang, Jinwei Yuan, Jiayi Li, Mengran Liang, Yitong Liu, Dongliang Xing, Liangru Yang
A photochemical approach toward RCOCF2-substituted pyrrolo­[1,2-a]­indolediones was developed by the radical cascade difluoroalkylation/cyclization reaction of unactivated 1-acryloyl-2-cyanoindoles with ethyl iododifluoroacetate or iododifluoramides under visible-light irradiation. This transition-metal- and photosensitizer-free protocol afforded diverse difluoroalkylated pyrrolo­[1,2-a]­indolediones in moderate to good yields under mild reaction conditions. Most appealingly, the reaction can proceed smoothly under sunlight irradiation, which opens a new avenue toward difluoroalkylated pyrrolo­[1,2-a]­indolediones.

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