Aerobic oxysulfonylation of alkynes in aqueous media: highly selective access to β-keto sulfones

The first application of inexpensive commercially available sulfinate salts to produce β-keto sulfones directly from alkynes via aerobic oxysulfonylation has been developed. It is a highly selective (undesired Glaser–Hay homo-coupling and ATRA process totally suppressed) general method of functional...

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Bibliographic Details
Published in:Tetrahedron letters 2014-04, Vol.55 (17), p.2845-2848
Main Authors: Singh, Atul K., Chawla, Ruchi, Yadav, Lal Dhar S.
Format: Article
Language:English
Subjects:
Alkynes
FeCl3/K2S2O8 catalysis
Formations
Media
Radical aerobic oxysulfonylation
Radicals
Sodium arenesulfinates
Sulfones
Tetrahedrons
β-Keto sulfones
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Summary:The first application of inexpensive commercially available sulfinate salts to produce β-keto sulfones directly from alkynes via aerobic oxysulfonylation has been developed. It is a highly selective (undesired Glaser–Hay homo-coupling and ATRA process totally suppressed) general method of functionalization of alkynes on water at room temperature involving FeCl3/K2S2O8 catalyzed formation of sulfonyl radicals from sulfinate salts.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.03.078