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- Title
Sulfonium Ylides by (3+2) Cycloaddition of Arynes with Vinyl Sulfides: Stereoselective Synthesis of Highly Substituted Alkenes.
- Authors
Li, Yuanming; Mück-Lichtenfeld, Christian; Studer, Armido
- Abstract
The reaction of in situ generated arynes with vinyl sulfides provides benzannulated sulfonium ylides in a (3+2) cycloaddition. Trapping of the intermediate ylides with electrophiles (proton transfer or a second aryne addition) and subsequent β-elimination give rise to di-, tri-, or tetrasubstituted alkenes with high stereoselectivity. Experimental studies and DFT calculations provide insight into the mechanisms of these cascade reactions.
- Subjects
SULFONIUM compounds; ARYNE; SULFIDES; ALKENES; NUCLEOPHILES
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 46, p14435
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201608144