Transition metal‐free cross‐coupling of benzothiophenes and styrenes in a stereoselective synthesis of substituted (E,Z)‐1,3‐dienes
journal contributionposted on 2019-07-09, 15:42 authored by Mindaugas Šiaučiulis, Nanna Ahlsten, Alexander P. Pulis, David J. Procter
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.
We thank The University of Manchester (Lectureship to A.P.P.), EPSRC [PhD studentship to M.S. and Established Career Fellowship to D.J.P. (EP/M005062/1)], and Eli Lilly (PhD CASE studentship to M.S.).
CitationAngewandte Chemie - International Edition, 2019, 58(26), pp. 8779-8783
Author affiliation/Organisation/COLLEGE OF SCIENCE AND ENGINEERING/Department of Chemistry
- AM (Accepted Manuscript)