alexa Expanding the scope of arylsulfonylacetylenes as alkynylating reagents and mechanistic insights in the formation of Csp2-Csp and Csp3-Csp bonds from organolithiums.


Organic Chemistry: Current Research

Author(s): Garca Ruano JL, Alemn J, Marzo L, Alvarado C, Tortosa M,

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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. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This article was published in Chemistry and referenced in Organic Chemistry: Current Research

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