The organic chemistry of silver acetylides

Silver acetylides are among the oldest organometallics known; however, their applications in organic chemistry remained scarce until very recently. Indeed, several reactions involving silver salts as catalyst or silver acetylides have been reported in the past five years. The extreme mildness and very low basicity of these nucleophilic reagents nicely complement the behavior of other alkynyl metals, rendering them very useful in various transformations, especially in the synthesis of complex molecules. Silver acetylides are now seen as promising tools in organic chemistry. This critical review focuses on this emerging field, and, with emphasis on mechanistic aspects, cover the synthesis of silver acetylides, their applications in organic chemistry and reactions involving silver salts as catalysts where silver acetylides are probable intermediates.