In summary, we successfully combined 1,2-radical migration (RaM) and excited-state Pd-catalyzed formal radical allylic alkylation to achieve C2-allylation of α-bromosugars with alkenes. Utilizing 1,1-disubstituted alkenes as allyl surrogates resulted in excellent atom economy and terminal olefin production via a sterically controlled β-H elimination pathway. This method features a wide substrate scope, enables late-stage functionalization, and streamlines the synthesis of C2-functionalized glycomimetics. Preliminary experimental and computational studies highlight the role of excited-state Pd-induced radical reactivity and reduced energy barriers for axial addition and terminal alkene formation. We anticipate that this reaction will broaden the applications of excited-state Pd-catalyzed allylic alkylation and provide rapid access to valuable glycomimetics.