To examine the feasibility of the proposed reaction, we began with an evaluation of various conditions, including different catalysts, ligands, temperatures, concentrations, and solvents (Scheme 1). Upon exposing acetylated 1-bromoglucose (1a, 1.00 equiv), N-(4-(prop-1-en-2-yl)phenyl)acetamide (2a, 3.00 equiv) to visible light irradiation from 36 W blue light-emitting diodes (LEDs) in the presence of Pd(PPh3)4 (5.00 mol%), Xantphos (6.00 mol%), K3PO4 (2.00 equiv) in benzene (0.01 M) at 90 ˚C, we observed the desired C2-allylated product 3a in 71% yield and a 6:1 ax:eq selectivity (entry 1). The essential role of Pd(PPh3)4 was highlighted by the absence of reaction without it and a significant yield decrease when substituted with Pd(OAc)2 (entries 2 & 3). The use of the Xantphos ligand enhanced the reactivity of the excited-state Pd-catalyst, with replacements, such as no Xantphos or BINAP, resulting in diminished yields of 35% and 53%, respectively (entries 4 & 5). Conventional photocatalysts like Ir(ppy)3 and Ru(bpy)3(PF6)2 showed low reactivity or no reaction (entries 6 & 7). The optimal results were achieved with K3PO4; alternatives like DIPEA or Cs2CO3 led to yields of 59% and 15%, respectively, and the absence of a base completely halted the reaction (entries 8-10). Using dioxane as a solvent or increasing the reaction concentration lowered the yields (entries 11 & 12). This decrease is attributed to the formation of a reduced side product when using dioxane and C1-coupling side products at high concentrations. The high temperature was crucial for radical migration and yield, as conducting the reaction at room temperature only produced a 6% yield (entry 13). Additionally, conducting the reaction in air or under dark conditions significantly hindered conversion (entries 14 & 15).