Tetrabutylammonium Iodide (TBAI) Catalyzed Electrochemical C-H Bond Activation of 2-Arylated N -Methoxyamides for the Synthesis of Phenanthridinones

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Abstract

An electrochemical method for the synthesis of phenanthridinones through constant-potential electrolysis (CPE) mediated by Bu 4 NI (TBAI) is reported. The protocol is metal and oxidant free, and proceeds with 100% current efficiency. TBAI plays a dual role as both a redox catalyst and a supporting electrolyte. The intramolecular C-H activation proceeds under mild reaction conditions and with a short reaction time through electrochemically generated amidyl radicals. The reaction has been scaled up to a gram level, showing its practicability, and the synthetic utility and applicability of the protocol have been demonstrated by a direct one-step synthesis of the bioactive compound phenaglaydon.

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Subramanian, K., Yedage, S. L., Sethi, K., & Bhanage, B. M. (2021). Tetrabutylammonium Iodide (TBAI) Catalyzed Electrochemical C-H Bond Activation of 2-Arylated N -Methoxyamides for the Synthesis of Phenanthridinones. Synlett, 32(10), 999–1003. https://doi.org/10.1055/a-1467-5585

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