Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 37, Pages 10417-10430Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201101047
Keywords
allylic compounds; iron; sulfones; sulfonylation; synthetic methods
Categories
Funding
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft
- Dr-Otto-Rohm-Gedachtnisstiftung
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Allyl sulfones are versatile intermediates in organic chemistry. The presence of two distinct functional groups sets the stage for a plethora of subsequent transformations. However, despite these advantages the preparation of regioisomerically enriched sulfones is not easy. The use of sulfinate salts as nucleophiles in substitutions is frequently accompanied by side reactions such as pi-bond migration, beta-elimination, and so on. Herein we present a preparatively simple way to synthesize a variety of different aryl or alkyl allyl sulfones starting from readily accessible allylic carbonates. By employing aryl or alkyl alpha-sulfonyl succinimides as sulfinate synthons, mild and regioselective ipso substitution of diverse allylic carbonates was realized.
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