Aerobic copper-catalyzed synthesis of (E)-alkenyl sulfones and (E)-β-halo-alkenyl sulfones via addition of sodium sulfinates to alkynes

Copper-catalyzed sulfonylation of alkynes using sodium sulfinates in air produced regio- and stereoselectively (E)-alkenyl sulfones. When a CuCl catalyst was employed, the hydrosulfonylation proceeded syn-selectively, and (E)-alkenyl sulfones were synthesized in excellent yields. In contrast, the re...

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Bibliographic Details
Published in:Tetrahedron 2014-03, Vol.70 (11), p.1984-1990
Main Author: Taniguchi, Nobukazu
Format: Article
Language:English
Subjects:
Alkyne
Alkynes
CATALYSTS
Copper catalyst
FABRICATION
Halides
JOINING
Sodium
Sodium sulfinate
Stereoselective addition
Sulfones
Sulfonylation
Synthesis (chemistry)
Tetrahedrons
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Summary:Copper-catalyzed sulfonylation of alkynes using sodium sulfinates in air produced regio- and stereoselectively (E)-alkenyl sulfones. When a CuCl catalyst was employed, the hydrosulfonylation proceeded syn-selectively, and (E)-alkenyl sulfones were synthesized in excellent yields. In contrast, the reaction using CuI catalyst produced (E)-β-haloalkenyl sulfones anti-selectively in the presence of potassium halides. Furthermore, the (E)-β-bromoalkenyl sulfones are possible to convert into various alkenyl sulfones by Suzuki–Miyaura coupling. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.01.071