1374637-83-8Relevant articles and documents
Expanding the scope of arylsulfonylacetylenes as alkynylating reagents and mechanistic insights in the formation of Csp2-Csp and Csp 3-Csp bonds from organolithiums
Garcia Ruano, Jose Luis,Aleman, Jose,Marzo, Leyre,Alvarado, Cuauhtemoc,Tortosa, Mariola,Diaz-Tendero, Sergio,Fraile, Alberto
, p. 8414 - 8422 (2012)
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. A calculated conclusion: A new transition-metal-free strategy for the synthesis of any kind of alkynyl derivatives in high yields in the reaction of organolithium species with arylsulfonylacetylenes is presented (see scheme). Theoretical calculations provide a rational explanation and suggest that association of the organolithium to the electrophile is a previous step of their intramolecular attack and is responsible for the "anti-Michael" reaction. Copyright
Arylsulfonylacetylenes as alkynylating reagents of C sp 2 -H bonds activated with lithium bases
Garcia Ruano, Jose Luis,Aleman, Jose,Marzo, Leyre,Alvarado, Cuauhtemoc,Tortosa, Mariola,Diaz-Tendero, Sergio,Fraile, Alberto
supporting information; experimental part, p. 2712 - 2716 (2012/04/17)
Chameleon: A new strategy for the synthesis of a wide variety of alkynyl derivatives by the reaction of substituted arylsulfonylacetylenes with organolithium species is described (see scheme). The high yields, the simplicity of the experimental procedure, the broad scope of this reaction, and the formation of Csp-C sp 2 bonds without using transition metals are the main features of this methodology. Copyright