Palladium-Catalyzed C-2 and C-3 Dual C–H Functionalization of Indoles: Synthesis of Fluorinated Isocryptolepine Analogues
Chen Chen, Yuebo Wang, Xiaonan Shi, Wan Sun, Jinghui Zhao, Yanping Zhu, Liying Liu, Bolin Zhu
Abstract
Here we report a protocol to synthesize diversiform fluorinated isocryptolepine analogues with potential biological activities in one step via directed C-2 and C-3 dual C-H functionalization of indoles. We also attempted to take into account fluorinated imidoyl chlorides as a novel kind of synthons in the directed C-H functionalization reactions. As a result, a variety of fluorinated isocryptolepine analogues were obtained in up to 96% yield. Moreover, we conducted control experiments to disclose the reaction mechanism.
Topics & Concepts
ChemistrySurface modificationPalladiumCatalysisCombinatorial chemistryDual (grammatical number)Dual roleStereochemistryMedicinal chemistryOrganic chemistryArtPhysical chemistryLiteratureSynthesis and bioactivity of alkaloidsCatalytic C–H Functionalization MethodsSynthesis and pharmacology of benzodiazepine derivatives