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Abstract:
The goal of the thesis was to explore the feasibility of C–H functionalization via
photochemically generated hydroperoxides. A practical method for the C–H functionalization of tetrahydrocarbazole derivatives via intermediate hydroperoxides with the aid of oxygen, visible light and catalytic amounts of a cheap Brønsted acid and a sensitizer has been developed. The reaction can be run in two steps or in a one-pot fashion, does not require synthetic oxidants, expensive metal catalysts, elevated temperatures or protective groups and can afford the coupling products in high yields within 5–6 hours. The developed
methodology has also been applied to the synthesis of some representative
pharmaceutically active compounds. The detailed investigations of the reaction
mechanism explained the exclusive C–H amination in the 1-position of the
tetrahydrocarbazole scaffold and also proved that a hydroperoxide moiety can be
used as leaving group under optimized acidic conditions.
