We report a direct and effective metal-free α-acylation of 2-oxindoles using C-acyl imidazolium salts as an acylating agent via C(O)−C bond cleavage. The mild reaction conditions, affordable base, additive-free and simple substrates make this methodology very attractive for easy access to 3-alkylidene oxindoles – privilege biologically active oxindole derivatives. The wide substrate scope and gram-scale preparation are notable features of this methodology. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim