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

Chroman-2-one derivatives are recognized as biologically relevant structures that exhibit notable pharmacological and biological properties, with C-4 alkylated derivatives being of particular interest. In the literature, methods have been described for the C-4 functionalization of coumarins using secondary and tertiary alkyl radicals, as well as aryl radicals, which are generated under reductive photocatalytic conditions.

In this work, a method is presented that enables the introduction of primary alkyl radicals, which are prepared through the oxidative proton-coupled electron transfer (PCET) ring opening of cycloalkanols under very mild reaction conditions. A broad substrate scope is demonstrated, and the methodology is shown to be amenable to large-scale synthesis under photo-flow conditions.

Furthermore, mechanistic investigations have been conducted, through which the occurrence of 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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