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Transition‐Metal‐Free Cross‐Coupling of Benzothiophenes and Styrenes in a Stereoselective Synthesis of Substituted ( E,Z )‐1,3‐Dienes
Author(s) -
Šiaučiulis Mindaugas,
Ahlsten Nanna,
Pulis Alexander P.,
Procter David J.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201902903
Subject(s) - benzothiophene , sulfonium , chemistry , stereoselectivity , hypervalent molecule , coupling reaction , transition metal , pummerer rearrangement , reagent , ligand (biochemistry) , organic chemistry , polymer chemistry , catalysis , thiophene , acetic anhydride , biochemistry , salt (chemistry) , receptor
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.