Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 26, Pages 8779-8783Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201902903
Keywords
ligand coupling; Pummerer reaction; sulfoxides; sulfur; sulfuranes
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Funding
- University of Manchester
- EPSRC [EP/M005062/1]
- Eli Lilly
- EPSRC [EP/M005062/1, 1712689, EP/P001386/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/M005062/1, EP/P001386/1] Funding Source: researchfish
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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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