4.4 Article

Stereoselective Synthesis of (E)-Alkenyl Sulfones from Alkenes or Alkynes via Copper-Catalyzed Oxidation of Sodium Sulfinates

Journal

SYNLETT
Volume -, Issue 9, Pages 1308-1312

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0030-1260544

Keywords

alkenyl sulfone; copper catalyst; sodium sulfinate; alkene; alkyne

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Alkenyl sulfones can be stereoselectively synthesized from alkenes or alkynes using sodium sulfinates. The reaction can be performed by a copper-catalyzed oxidation of sodium sulfinates in air. The reaction of alkenes gives (E)-alkenyl sulfones via anti addition of sulfonyl cation and elimination process. Furthermore, the employment of alkynes produces (E)-beta-haloalkenyl sulfones in the presence of potassium halides.

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