Gold‐Catalyzed Cycloisomerization of Sulfur Ylides to Dihydrobenzothiepines
| Autor: | Rafael Gomes, Thomas Alexander Stephens, Iakovos Saridakis, Nuno Maulide, Rik Oost, Christian Knittl-Frank, Alberto Oppedisano, Antonio Misale, James D. Neuhaus |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Sulfide
rearrangement chemistry.chemical_element benzothiepines 010402 general chemistry alkynes 01 natural sciences Medicinal chemistry Catalysis Cycloisomerization Atom economy Moiety Reactivity (chemistry) chemistry.chemical_classification Nucleophilic addition 010405 organic chemistry Communication Organic Chemistry General Chemistry gold Sulfur Communications 0104 chemical sciences chemistry Ylide Catalysis | Hot Paper sulfonium ylides |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | 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. Readily available S‐homopropargyl sulfonium ylides are transformed to substituted dihydrobenzo[b]thiepines under AuI catalysis. This atom‐efficient transformation takes place under very mild conditions at ambient temperature and proceeds through a charge‐accelerated sulfonium [3,3]‐sigmatropic rearrangement. |
| Databáze: | OpenAIRE |
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