Gold-Catalyzed Cycloisomerization of Sulfur Ylides to Dihydrobenzothiepines.
Christian Knittl-FrankIakovos SaridakisThomas StephensRafael F A GomesJames NeuhausAntonio MisaleRik OostAlberto OppedisanoNuno MaulidePublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2020)
The metal-promoted nucleophilic addition of sulfur ylides to π-systems is a well-established reactivity. However, the driving force of such transformations, elimination of a sulfide moiety, entails stoichiometric byproducts making them unfavorable in terms of atom economy. In this work, a new take on sulfur ylide chemistry is reported, an atom-economical gold(I)-catalyzed synthesis of dihydrobenzo[b]thiepines. The reaction proceeds under mild conditions at room temperature.