With optimized conditions in hand, we studied first the scope of arylcyclopropanes (Scheme 2A). As expected, electron-rich substituents were required to promote the reaction: oxyalkynylation products 3a-c bearing a methoxy or an ethoxy substituent were obtained in 51-68% yield, whereas a tert-butyl substituent gave 3d in only 15% yield and no product was obtained for an unsubstituted benzene ring (3e). For 3a and 3b, the yields obtained were comparable or slightly superior to the photocatalytic method developed by Zuo and Studer. 13 However, the photocatalyst approach is superior for less electron-rich substrates not accessible via direct photoexcitation of EBXs: Products 3d and 3e where obtained in 52% and 40% respectively using an acridinium dye as photocatalyst. A methyl group in ortho position was well tolerated to give product 3f. However, no product 3g was obtained with two ortho methyl groups. Surprisingly, C-H alkynylation product 4a was isolated in 85% yield instead. In presence of a methoxy group, an electron-deficient fluoro substituent was tolerated to give product 3h in 46% yield. Starting from -substituted cyclopropanes, products 3i and 3j were obtained in 70% and 54% yield with selective attack of the iodobenzoate at the most encumbered position. We then examined the scope of EBX reagents, considering that only aryl-substituted EBXs are photoactive (Scheme 2B). 14 A tolyl-substituted EBX gave 3k in 45% yield. Introduction of a para-trifluoromethyl or a chloro group on the aryl ring of the alkyne led to 3l and 3m in 63% yield. Fluoro substituents were also tolerated, but gave only moderate yields of 3n and 3o. These results contrasted with our previous work were only Phand tolyl-EBX gave useful yields of products. 14 Scheme 2 Scope of the oxyalkynylation of arylcyclopropanes. Reaction Conditions: 0.2 mmol 1a (1 equiv), 0.5 mmol 2 (2.5 equiv), two Kessil lamps (440 nm, 2x40 W), in 2 mL CHCl3. Isolated yield after column chromatograpy is given. a Yield reported in Ref. 13 using 4-CzIPN as photocatalyst and BI-OAc as additive. b Yield using Ph-Acr-MesBF4 as photocatalyst.