A Regioselective and efficient synthesis of α,α-diiodo-α′-acetoxyketones as well as α,α-dibromo-α′ -acetoxyketones has been achieved from the propargylic acetates and N-iodo(bromo)succinimides in the absence of any added promoters. This transformation is very general and shown compatibility for all structural types of propargylic acetates with terminal alkyne unit, such as tertiary- (aryl-aryl; aryl-alkyl; alkyl-alkyl), secondary- (aryl; alkyl), primary-; and hence provided access to structurally divergent and highly important halogenated building blocks. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim