Proton-Coupled Electron Transfer Processes in the Decarboxylative Synthesis of C-4 Substituted Chroman-2-Ones

Chroman-2-one derivatives are biologically relevant structures that present interesting pharmacological and biological properties, being the C-4 alkylated derivatives of particular interest. The methods described in the literature allow the C-4 functionalization of coumarins with secondary and tertiary alkyl radicals, as well as aryl radicals produced under reductive photocatalytic conditions. Herein, we present a method that allows the introduction of primary alkyl radicals prepared through the oxidative-PCET ring opening of cycloalkanols under very mild reaction conditions. The method presents a broad scope and can be carried out on a large scale under photo-flow conditions. Moreover, mechanistic investigations allow the corroboration of decarboxylation under polar conditions.

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