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One-pot synthesis of sulfonyl dibenzosuberdiones via In(OTf)3-promoted double Friedel-Crafts reactions of oxygenated arylacetic acids with β-arylvinyl sulfones. 2023
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan. mychang@kmu.edu.tw.
Under open-vessel atmosphere conditions, a one-pot easy-to-operate method for the construction of diverse sulfonyl dibenzosuberdiones is developed via In(OTf)3-promoted tandem double Friedel-Crafts reactions of oxygenated arylacetic acids with β-arylvinyl sulfones. A plausible mechanism is proposed and discussed in detail. This protocol allows for highly effective sequential intermolecular Michael addition, intramolecular ring-closure and α-benzylic oxidation via the formation of two carbon-carbon single (C-C) bonds and one carbon-oxygen double (CO) bond.
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