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Gold-Catalyzed Cycloisomerization of Sulfur Ylides to Dihydrobenzothiepines.

ABSTRACT: The metal-promoted nucleophilic addition of sulfur ylides to ?-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.

SUBMITTER: Knittl-Frank C

PROVIDER: S-EPMC7496544 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Gold-Catalyzed Cycloisomerization of Sulfur Ylides to Dihydrobenzothiepines.

Knittl-Frank Christian C Saridakis Iakovos I Stephens Thomas T Gomes Rafael R Neuhaus James J Misale Antonio A Oost Rik R Oppedisano Alberto A Maulide Nuno N

Chemistry (Weinheim an der Bergstrasse, Germany) 20200608 48

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. ...[more]

PMID: 32227380

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