Gold- or Platinum-Catalyzed Synthesis of Sulfur Heterocycles: Access to Sulfur Ylides without Using Sacrificial Functionality

It′s no sacrifice: Alkynes have been used as direct precursors to sulfur ylides under gold or platinum π‐acid catalysis in an atom‐economic manner. An intramolecular redox reaction between an alkyne group with a tethered sulfoxide unit generates a sulfur ylide, which undergoes 2,3‐sigmatropic rearra...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2009-10, Vol.48 (44), p.8372-8375
Main Authors: Davies, Paul W, Albrecht, Sébastien J.-C
Format: Article
Language:English
Subjects:
alkynes
gold
homogeneous catalysis
sulfur heterocycles
ylides
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Summary:It′s no sacrifice: Alkynes have been used as direct precursors to sulfur ylides under gold or platinum π‐acid catalysis in an atom‐economic manner. An intramolecular redox reaction between an alkyne group with a tethered sulfoxide unit generates a sulfur ylide, which undergoes 2,3‐sigmatropic rearrangement. Acyclic substrates are cycloisomerized to afford functionalized dihydrothiophenones (see scheme) and dihydrothiopyranones.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200904309