Premium
Sulfonium Ylides by (3+2) Cycloaddition of Arynes with Vinyl Sulfides: Stereoselective Synthesis of Highly Substituted Alkenes
Author(s) -
Li Yuanming,
MückLichtenfeld Christian,
Studer Armido
Publication year - 2016
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.201608144
Subject(s) - aryne , sulfonium , stereoselectivity , cycloaddition , electrophile , chemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , salt (chemistry)
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.