Hexafluorosilicic Acid as a Novel Reagent for the Desilylation of Silylacetylenes: Application in Sequential Sonogashira Coupling and Click Reaction, Ádám Sinai, Ádám Mészáros, Ádám Balogh, Márton Zwillinger, Zoltán Novák, Synthesis 2017, 49, 2374-2388. DOI: 10.1055/s-0036-1588981 | [Full Text Link] [Supp. Info. Link]

Key words: alkynes - azides - cycloaddition - click reaction - cross-coupling­ - fluoride - palladium - heterocycles

Hexafluorosilicic acid was utilized as a novel, cheap, readily available, and environmentally benign alternative reagent for the desilylation of 1-trimethylsilylacetylenes. The applicability of the aqueous solution of the hexafluorosilicic acid was demonstrated in the sequential coupling of aryl halides and ethynyltrimethylsilane to afford internal acetylenes, benzofurans, and triazoles in one-pot Sonogashira–Sonogashira­ and Sonogashira–CuAAC reactions.