Science Faculty

Expanding the Scope of Arylsulfonylacetylenes as Alkynylating Reagents and Mechanistic Insights in the Formation of Csp2-Csp and Csp3-Csp Bonds from Organolithiums

Author/s

García Ruano, J. L.; Alemán, J.; Marzo, L.; Alvarado, C.; Tortosa, M.; Díaz-Tendero, S.; Fraile, A.

Año de edición

2012

Referencia completa

Chem. Eur. J. 2012, 18, 8414-8422. DOI: 10.1002/chem.201200939

Resumen

We describe the unexpected behavior of the arylsulfonylacetylenes, which suffer an “anti‐Michael” addition of organolithiums producing their alkynylation under very mild conditions. The broad scope, excellent yields, and simplicity of the experimental procedure are the main features of this methodology. A rational explanation of all these results can be achieved by theoretical calculations, which suggest that the association of the organolithiums to the electrophile is a previous step of their intramolecular attack and is responsible for the unexpected “anti‐Michael” reactions observed for substituted sulfonylacetylenes.

Otros datos de interés

Destacada por Chem. Eur. J. como “VIP article” y como “Cover Picture 2012, Vol. 18, issue 27.