Vinyl nosylates as partner in copper and silver co-catalyzed Sonogashira cross-coupling reactions

Vinyl nosylates, readily obtained from β-dicarbonyl derivatives, could be efficiently engaged in Sonogashira cross-coupling reactions, either cocatalyzed by copper or silver salts. The para-nitrobenzenesulfonate (nosylate) group allows this coupling to be performed under very mild conditions (room t...

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Bibliographic Details
Published in:Tetrahedron 2018-12, Vol.74 (50), p.7111-7119
Main Authors: Cheval, Nicolas P., Hoffmann, Barbara, Dikova, Anna, Sirindil, Fatih, Bertus, Philippe, Blanc, Aurélien, Weibel, Jean-Marc, Pale, Patrick
Format: Article
Language:English
Subjects:
Chemical Sciences
Cross-coupling
Palladium
para-Nitrobenzenesulfonate
Sonogashira
Vinyl nosylates
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Summary:Vinyl nosylates, readily obtained from β-dicarbonyl derivatives, could be efficiently engaged in Sonogashira cross-coupling reactions, either cocatalyzed by copper or silver salts. The para-nitrobenzenesulfonate (nosylate) group allows this coupling to be performed under very mild conditions (room temperature). These new leaving group and mild conditions could be applied to the synthesis of acetylenic coumarinyl derivatives and to the total synthesis of an acetylenic monoterpene natural product, named cleviolide. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.10.017