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- Title
Expanding the Scope of Arylsulfonylacetylenes as Alkynylating Reagents and Mechanistic Insights in the Formation of Csp<sup>2</sup>Csp and Csp<sup>3</sup>Csp Bonds from Organolithiums.
- Authors
García Ruano, José Luis; Alemán, José; Marzo, Leyre; Alvarado, Cuauhtémoc; Tortosa, Mariola; Díaz-Tendero, Sergio; Fraile, Alberto
- Abstract
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.
- Publication
Chemistry - A European Journal, 2012, Vol 18, Issue 27, p8414
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201200939