Synthesis of Polysubstituted Olefins by Pd-Catalyzed Cross-Coupling Reaction of Tosylhydrazones and Aryl Nonaflates

José Barluenga*, Lucía Florentino, Fernando Aznar and Carlos Valdés*

*Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, c/Julián Clavería 8, 33006, Oviedo, Spain, Email: barluengauniovi.es, acvguniovi.es

J. Barluenga, L. Florentino, F. Aznar, C. Valdes, Org. Lett., 2011, 13, 510-513.

DOI: 10.1021/ol102884g

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Abstract

Aryl nonaflates are employed as electrophiles in the Pd-catalyzed cross-coupling with tosylhydrazones affording highly substituted olefins. Addition of LiCl and the presence of small amounts of water are required to accomplish the coupling successfully. Under the optimized conditions, the reactions proceed with high yield and also high stereoselectivity depending on the nature of the coupling partners.

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Key Words

Alkenylations

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ID: J54-Y2011-0230