Organic Chemistry

Boron-promoted Deprotonative Conjugate Addition: Development of Geminal diborons as Versatile Soft Pronucleophiles and Acyl An-ion Equivalents



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.


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Supplementary material

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Supporting Information
Experimental procedures, characterization data, NMR spectra (PDF).