Multicomponent　reactions　(MCRs)　facilitate　the　rapid　and　diverse　construction　of　molecular　scaffolds　with　modularity　and　step　economy.　In　this　work,　engagement　of　boronic　acids　as　carbon　nucleophiles　culminates　in　a　Passerini-type　three-component　coupling　reaction　towards　the　synthesis　of　an　expanded　inventory　of　alpha　-hydroxyketones　with　skeletal　diversity.　In　addition　to　the　appealing　features　of　MCRs,　this　protocol　portrays　good　functional　group　tolerance,　broad　substrate　scope　under　mild　conditions　and　operational　simplicity.　The　utility　of　this　chemistry　is　further　demonstrated　by　amenable　modifications　of　bioactive　products　and　pharmaceuticals　as　well　as　in　the　functionalization　of　products　to　useful　compounds.　Multicomponent　reactions　enable　the　rapid　construction　of　diverse　molecular　scaffolds　with　modularity　and　step　economy.　In　this　work,　the　authors　report　the　use　of　boronic　acids　as　carbon　nucleophiles　in　a　Passerini-type　three-component　coupling　reaction　towards　an　expanded　inventory　of　alpha　-hydroxyketones.