Conjugate addition of α-boron stabilized carbanions is an underexplored reaction modality. Existing methods require deborylation of geminal di/triboryl alkanes and/or the presence of additional activating groups. We report the 1,4-addition of α,α-diboryl carbanions generated via deprotonation of corresponding geminal diborons. The methodology enabled a general route to highly substituted and synthetically useful γ,γ-diboryl ketones. The development of geminal diborons as soft pronucleophiles also enabled their use as acyl anion equivalents via one-pot tandem conjugate addition-oxidation sequence.