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Cover Feature: Gold‐Catalyzed Cycloisomerization of Sulfur Ylides to Dihydrobenzothiepines (Chem. Eur. J. 48/2020)
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.202003046
Subject(s) - sulfonium , cycloisomerization , ylide , sulfur , moiety , catalysis , chemistry , reactivity (psychology) , sulfide , alkylation , medicinal chemistry , organic chemistry , combinatorial chemistry , medicine , salt (chemistry) , alternative medicine , pathology
Many reactions of sulfonium ylides suffer from stoichiometric waste production through release of the sulfur moiety. An atom‐economical synthesis of heterocycles has now been developed, which showcases a novel mode of sulfonium ylide reactivity. Treatment of S‐homopropargyl sulfonium ylides with a gold catalyst under mild conditions results in an atom‐economical, charge‐accelerated sulfonium [3,3]‐sigmatropic rearrangement, giving access to a variety of novel dihydrobenzo[b]thiepines without release of any sulfur by‐product. More information can be found in the Communication by N. Maulide et al. on page 10972).