Since a nucleophilic sp² boron species can be generated in situ under the combined action of an inorganic base, B₂pin₂ and methanol, research on base-promoted nucleophilic borylation of unsaturated compounds has attracted significant attention. A series of multi-borylated compounds, such as alkyl 1,2-bis(boronates), gem-diborylalkanes, and 1,1,2-tris(boronates), are constructed based on this strategy. These multi-borylated compounds can in turn undergo selective protodeboronation, creating a variety of useful boron-containing compounds. This Feature article documents the development of base-promoted domino-borylation-protodeboronation (DBP) strategies and their applications in organic synthesis.