Environmentally
friendly and highly regioselective C-3 dichlorination
and C-2 oxidation of N-substituted indoles have been established using
NaCl as a chlorine source and H2O as an oxygen source.
A series of 3,3-dichloro-2-oxindoles were obtained in moderate to
excellent yields. The gram-scale synthesis and derivatization reaction
were explored. The possible mechanism for this reaction was elucidated.
An efficient and convenient method for electrochemically oxidative dichlorination or dibromination of 8‐aminoquinolines on C5 and C7 positions using N‐halosuccinimides (NCS and NBS) as the halogen source was described. Substrates with various functional groups were transformed smoothly and the halogenated products were obtained in good to excellent yields. These transformations feature transition‐metal‐free, oxidant‐free, and short reaction time.
An efficient electrolyte‐triggered trifluoromethylation and halogenation at C5 position of 8‐aminoquinoline derivatives was developed, affording the C−H functionalization products in moderate to excellent yields. Furthermore, the mild and green reactions had lower energy consumption and shorter times. Most importantly, both transition‐metal catalysts and oxidants were avoided.
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