Boron-Promoted Deprotonative Conjugate Addition: Geminal Diborons as Soft Pronucleophiles and Acyl Anion Equivalents

Lucia Wang, Shengjia Lin, Emmanuel Santos, Jenna Pralat, Kaylyn Spotton, Abhishek Sharma

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

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.

Original languageEnglish
Pages (from-to)9896-9906
Number of pages11
JournalJournal of Organic Chemistry
Volume87
Issue number15
DOIs
StatePublished - 5 Aug 2022

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