Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy

Craig Buxton, David C. Blakemore, John Bower

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

15 Citations (Scopus)
199 Downloads (Pure)

Abstract

Nickel-catalyzed coupling of benzyl acrylates with activated ketones and imines provides γ-butyrolactones and lactams, respectively. The benzyl alcohol byproduct released during the lactonization/lactamization event is relayed to the next cycle where it serves as the reductant for C−C bond formation. This strategy represents a conceptually unique approach to transfer-hydrogenative C−C bond formation, thus providing examples of reductive heterocyclizations where hydrogen embedded within an alcohol leaving group facilitates turnover.
Original languageEnglish
Pages (from-to)13824-13828
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number44
Early online date4 Sep 2017
DOIs
Publication statusPublished - 23 Oct 2017

Structured keywords

  • BCS and TECS CDTs

Keywords

  • alcohols
  • lactones
  • nickel
  • spiro compounds
  • transfer hydrogenation

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