Tailored Palladium Catalysts for Selective Synthesis of Conjugated Enynes by Monocarbonylation of 1,3-Diynes

Jiawang Liu, Ji Yang, Carolin Schneider, Robert Franke, Ralf Jackstell, Matthias Beller

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

For the first time, the monoalkoxycarbonylation of easily available 1,3-diynes to give synthetically useful conjugated enynes has been realized. Key to success was the design and utilization of the new ligand 2,2′-bis(tert-butyl(pyridin-2-yl)phosphanyl)-1,1′-binaphthalene (Neolephos), which permits the palladium-catalyzed selective carbonylation under mild conditions, providing a general preparation of functionalized 1,3-enynes in good-to-high yields with excellent chemoselectivities. Synthetic applications that showcase the possibilities of this novel methodology include an efficient one-pot synthesis of 4-aryl-4H-pyrans as well as the rapid construction of various heterocyclic, bicyclic, and polycyclic compounds.

Original languageEnglish
Pages (from-to)9032-9040
Number of pages9
JournalAngewandte Chemie International Edition in English
Volume59
Issue number23
DOIs
StatePublished - 2 Jun 2020
Externally publishedYes

Keywords

  • P ligands
  • conjugated enynes
  • monocarbonylation
  • palladium
  • selectivity

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