Ligand-Controlled Palladium-Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α-Methylene-β-Lactones

Yao Ge, Fei Ye, Jiawang Liu, Ji Yang, Anke Spannenberg, Haijun Jiao, Ralf Jackstell, Matthias Beller

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The first general and regioselective Pd-catalyzed cyclocarbonylation to give α-methylene-β-lactones is reported. Key to the success for this process is the use of a specific sterically demanding phosphine ligand based on N-arylated imidazole (L11) in the presence of Pd(MeCN)2Cl2 as pre-catalyst. A variety of easily available alkynols provide under additive-free conditions the corresponding α-methylene-β-lactones in moderate to good yields with excellent regio- and diastereoselectivity. The applicability of this novel methodology is showcased by the direct carbonylation of biologically active molecules including natural products.

Original languageEnglish
Pages (from-to)21585-21590
Number of pages6
JournalAngewandte Chemie International Edition in English
Volume59
Issue number48
DOIs
StatePublished - 23 Nov 2020
Externally publishedYes

Keywords

  • alkynol
  • carbonylation
  • catalysis
  • palladium
  • phosphine
  • α-methylene-β-lactone

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