CHAPTER 15: Transition Metal-catalysed Nucleophilic Additions of Terminal Alkynes in Water: Development and Synthetic Utility

This chapter summarises the literature concerning the nucleophilic addition of terminal alkynes to a varied scope of unsaturated electrophiles to prepare alkynylated molecules. Unlike classical methods that achieve this transformation by employing stoichiometric quantities of highly reactive metal acetylides and therefore require inert and anhydrous conditions, the transition metal-catalysed reactions described herein can be conducted in water, a benign and readily available solvent. In addition to overviewing transformations for the one-step addition of terminal alkynes to electrophiles, multi-component and tandem reactions are addressed. Furthermore, to offer a more complete resource for chemists seeking more sustainable routes to synthetic targets, a brief survey of the synthetic utility of the alkynylated reaction products is provided.