We initiate the investigation by surveying the coupling between an activated amide and a 1-substituted cyclopropanol. In particular, 2-benzoylisoindoline-1,3-dione (1a μP ), an N-acyl-phthalimide with a twisted amide bond, is employed to react with 1-(4methoxyphenyl)cyclopropan-1-ol (2d) under Pd catalysis. A comprehensive screening allows the identification of a catalyst combination of 10 mol % Pd(OPiv)2, 20 mol % PCy3, 1.0 equiv Et3N, and achievement of a maximum yield of 62% for 3ad after 16 h of 90 o C reaction in toluene. With this encouraging result in hand and in pursuit of a lower catalyst loading, we switch the amide from 1a μP to 1-benzoylpiperidine-2,6-dione (1a), an N-acyl-glutarimide with a more distorted amide bond and a supposedly higher reactivity. A round of focused sifting of the reaction conditions affords an optimized yield of 68% under catalysis with 5 mol % Pd(acac)2 and 10 mol % PCy3 (80 o C, toluene, 16 h). The full elimination of the stoichiometric use of an acid or base as the additive is consistent with the involvement of a thermodynamically favored acid-base proton transfer process. Indeed, none of the supplementary additives tested could contribute to a further enhancement of the yield. PCy3 and toluene prove to be superior to other ligands and solvents.