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

Nobukazu Taniguchi*

*Department of Chemistry, Fukushima Medical University, Fukushima 960-1295, Japan, Email: tanigutifmu.ac.jp

N. Taniguchi, Synlett, 2011, 1308-1312.

DOI: 10.1055/s-0030-1260544

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Abstract

Alkenyl sulfones can be stereoselectively synthesized from alkenes or alkynes using sodium sulfinates in the presence of CuI-bpy as catalyst and oxygen. The reaction of alkenes gives (E)-alkenyl sulfones via anti addition of the sulfonyl cation followed by an elimination process. Furthermore, the employment of alkynes produces (E)-β-haloalkenyl sulfones in the presence of potassium halides.

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Copper-Catalyzed Oxidative Hydrosulfonylation of Alkynes Using Sodium Sulfinates in Air

N. Taniguchi, Synlett, 2012, 23, 1245-1249.

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Key Words

alkenyl sulfones, copper catalyst, sodium sulfinates, alkenes, alkynes, oxygen

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ID: J60-Y2011-1660