Cover Picture: Expanding the Scope of Arylsulfonylacetylenes as Alkynylating Reagents and Mechanistic Insights in the Formation of Csp2Csp and Csp3Csp Bonds from Organolithiums (Chem. Eur. J. 27/2012)

Abstract

Transition-metal-free alkynylation of Csp2 or Csp3 atoms in the reaction of sulfonylacetylenes with organolithium species is described by J. L. García Ruano, J. Alemán, et al. on page 8414 ff. Rather than the expected β-attack, α-attack of the nucleophiles occurs as a result of the chameleonic behavior of the sulfonyl group, which is able to coordinate to the lithium species in an “anti-Michael” addition reaction.