Although the direct light-mediated oxidation of arylcyclopropanes has been reported with nitrogen-based and chloride radicals, 15 alkynylation could not be achieved so far in absence of a photocatalyst. Herein, we report the first ring-opening oxyalkynylation of aryl cyclopropanes through the direct photoexcitation of EBX reagents (Scheme 1D). The 1,3-oxyalkynylation products were obtained with full regioselectivity, in yields comparable to those of photocatalytic methods. The same conditions were also used for the 1,3-oxyalkynylation of aminocyclopropanes and the 1,2oxyalkynylation of styrenes. In addition, the reaction outcome could be changed from C-C to C-H alkynylation in dependence of the aryl group on the cyclopropane.