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Gold‐Catalyzed Cycloisomerization of Sulfur Ylides to Dihydrobenzothiepines
Author(s) -
KnittlFrank Christian,
Saridakis Iakovos,
Stephens Thomas,
Gomes Rafael,
Neuhaus James,
Misale Antonio,
Oost Rik,
Oppedisano Alberto,
Maulide Nuno
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000622
Subject(s) - cycloisomerization , sulfur , ylide , catalysis , moiety , reactivity (psychology) , chemistry , sulfide , nucleophile , atom economy , stoichiometry , atom (system on chip) , organic chemistry , photochemistry , medicine , alternative medicine , pathology , computer science , embedded system
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.