Proton-Coupled Electron Transfer Processes in the Decarboxy-lative Synthesis of C-4 Substituted Chroman-2-ones

Chroman-2-one derivatives are considered biologically relevant structures due to their interesting pharmacological and biological properties, with particular interest being placed on the C-4 alkylated derivatives. In the literature, methods have been described that allow the functionalization of coumarins at the C-4 position using secondary and tertiary alkyl radicals, as well as aryl radicals, which are generated under reductive photocatalytic conditions. Herein, a method is presented in which primary alkyl radicals are introduced through the oxidative-PCET ring opening of cycloalkanols under very mild reaction conditions. A broad scope is demonstrated by the method, and large-scale application is enabled under photo-flow conditions. Furthermore, mechanistic investigations have been conducted, by which the decarboxylation under polar conditions has been corroborated.

• Kowalska, E
• Carli, B
• Puerta, L
• Alemán, J
• Albrecht, A

• Lodz University of Technology

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