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

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  • Authors:
  • Mindaugas Siauciulis
  • Nanna Ahlsten
  • Alexander Pulis
  • David Procter

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.

Bibliographical metadata

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

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