24.4.3.5 1-(Organosulfanyl)-, 1-(Organoselanyl)-, and 1-(Organotellanyl)alk-1-ynes (Update 2018)

Abstract

This chapter is an update to the earlier Science of Synthesis review (Section 24.4.3) describing the synthesis of 1-(organochalcogeno)alk-1-ynes, where the chalcogen is sulfur, selenium, or tellurium. It covers the literature from the period 2005–2016. Many of the approaches to these molecules involve reaction of an acetylide with a suitable chalcogen source, but other methods include the formation of the C≡C bond by elimination, the reaction of a chalcogenide species with alkynes bearing a leaving group at the alkyne terminus, and various types of coupling reactions. Also covered in this update are the recent applications of the title compounds. The wide range of reactions reported shows the importance of these molecules as building blocks and key intermediates in organic synthesis.