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 iau
iulis Nanna Ahlsten Alexander P Pulis David J Procter |
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Institution: | Mindaugas Šiaučiulis,Nanna Ahlsten,Alexander P. Pulis,David J. 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. |
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Keywords: | Ligandenkupplung Pummerer-Reaktion Schwefel Sulfoxide Sulfurane |
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