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A regioselective direct alkylation of coumarins at C-3 via cross-dehydrogenative coupling of unactivated Csp 2–Csp 3 bonds is developed. This protocol employs tert-butyl hydroperoxide as the sole reagent of the reaction to combine coumarins and ethers in reasonable yields under metal- and solvent-free reaction conditions. This protocol also worked well with coumarin-3-carboxylic acids to unveil a rare instance of a catalyst-free tandem alkylation/decarboxylation reaction with conservation of the double bond. • For reproduction of material from NJC: Reproduced from Ref.