Simple and practical one-step synthesis of new 1,3-dienic δ-sultones from terminal alkynes and some synthetic applications of these compounds

Abstract

1,3-Dienic δ -sultones 4,6-diaryl-[1,2]oxathiine 2,2-dioxides were synthesized via a one-step reaction of arylalkynes with dioxane sulfotrioxide. The reactivity of various alkynes in this reaction was investigated. The resulting sultones were brominated with Br₂ or N-bromosuccinimide regioselectively α to sulfur and subsequently coupled with phenylacetylene using Sonogashira conditions.

Keywords:

• alkynes
• dioxane sulfotrioxide
• δ-sultones
• bromination
• Sonogashira coupling

Acknowledgements

Financial support of this work by the DFG (ME 776/15-2) and the Rosa-Luxemburg-Foundation is gratefully acknowledged.

Notes

Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 776086 (6b), CCDC 776085 (8a), CCDC 776084 (8c).

Additional information

Notes on contributors

Olga Kataeva

X-ray diffraction analysis.