Photoredox-Enabled Synthesis of alpha-Alkylated Alkenylammonium Salts

Photoredox-Enabled Synthesis of a-Alkylated Alkenylammonium Salts: R. Tonedachi, A. Yoshita, Y. Sakakibara, K. Murakami
Synthesis 2024, DOI: 10.1055/a-2302-5887

Quaternary ammonium salts find extensive use as surfactants, pharmaceuticals, and catalysts. Their synthesis is generally accomplished via quaternarization of tertiary amines (Menshutkin reaction), which is a practical method for the synthesis of tetraalkylammonium salts but is way less effective for the synthesis of alkenylammonium salts. Recently, the group of Professor Kei Murakami (Kwansei Gakuin University, Sanda, Japan) reported a photoredox-enabled strategy for the synthesis of a-alkylated alkenylammonium salts, taking place through the generation of a highly reactive a-ammoniovinyl radical.


Professor Murakami said: “We demonstrated the potential of photoredox-catalyzed debrominative alkylation of a-brominated alkenylammonium salts. Our methodology enables the synthesis of various unprecedented a-alkylated alkenylammonium salts.”

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