Boron-Promoted Deprotonative Conjugate Addition: Geminal Diborons as Soft Pronucleophiles and Acyl Anion Equivalents
Lucia Wang, Sheng‐Jia Lin, Emmanuel Santos, Jenna Pralat, Kaylyn Spotton, Abhishek Sharma
Abstract
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 the corresponding geminal diborons. The methodology provided 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 a one-pot tandem conjugate addition-oxidation sequence.
Topics & Concepts
ChemistryGeminalConjugateBoronEquivalentIonBOROMedicinal chemistryOrganic chemistryBiochemistryMathematical analysisMathematicsOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsChemical Synthesis and Analysis