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

07 March 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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 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.

Supplementary materials

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