Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans

Yahui Wang, Adam Noble, Christopher Sandford, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

36 Citations (Scopus)
316 Downloads (Pure)

Abstract

In the presence of trifluoromethylsulfonium reagents, boronate complexes derived from 2-lithio furan and non-racemic secondary and tertiary alkyl or aryl boronic esters undergo deborylative three-component coupling to give the corresponding 2,5-disubstituted furans with excellent levels of enantiospecificity. The process proceeds via the reaction of boronate complexes with a trifluoromethyl radical, which triggers 1,2-metallate rearrangement upon single-electron oxidation. Alternative electrophiles can also be used in place of trifluoromethylsulfonium reagents to effect similar three-component coupling reactions.
Original languageEnglish
Pages (from-to)1810-1814
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number7
Early online date30 Jan 2017
DOIs
Publication statusPublished - 6 Feb 2017

Keywords

  • boronic esters
  • cross-coupling
  • furans
  • stereospecificity
  • trifluoromethylation

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