Transition‐Metal‐Free Cross‐Coupling of Benzothiophenes and Styrenes in a Stereoselective Synthesis of Substituted (E,Z)‐1,3‐Dienes

Mindaugas Siauciulis, Nanna Ahlsten, Alexander Pulis, David Procter

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Abstract

A transition metal‐free one‐pot stereoselective approach to substituted (E,Z)‐1,3‐dienes was developed by using an interrupted Pummerer reaction/ligand‐coupling strategy. Readily available benzothiophene S‐oxides, which can be conveniently prepared by oxidation of the parent benzothiophenes, undergo Pummerer coupling with styrenes. Reaction of the resultant sulfonium salts with alkyllithium/magnesium reagents generates underexploited hypervalent sulfurane intermediates that undergo selective ligand coupling, resulting in dismantling of the benzothiophene motif and the formation of decorated (E,Z)‐1,3‐dienes.
Original languageEnglish
Pages (from-to)8779-8783
JournalAngewandte Chemie. International Edition
Volume58
Issue number26
Early online date7 Jun 2019
DOIs
Publication statusPublished - 13 Jun 2019

Keywords

  • Ligand Coupling
  • Pummerer reaction
  • sulfoxides
  • sulfur
  • sulfuranes

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