title: Sulfonium Ylides by (3+2) Cycloaddition of Arynes with Vinyl Sulfides: Stereoselective Synthesis of Highly Substituted Alkenes.
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.
authors.affiliation: Westfälische Wilhelms-Universität, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany.
authors.forename: Yuanming
authors.initials: Y
authors.lastname: Li
authors.affiliation: Westfälische Wilhelms-Universität, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Mück-Lichtenfeld
authors.affiliation: Westfälische Wilhelms-Universität, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany. studer@uni-muenster.de.
authors.forename: Armido
authors.identifier: 0000-0002-1706-513X
authors.initials: A
authors.lastname: Studer
keywords: alkenes; arynes; cycloaddition; sulfonium ylides; synthetic methods