Oxidative trifluoromethyl(thiol/selenol)ation of terminal alkynes: An overview

The development of mild, selective, and practical methods for the introduction of fluorine atom and fluorine-containing functional groups into organic molecules has received tremendous attention because many pharmaceuticals, agrochemicals, refrigerants, and high performance materials (e.g., plastics, elastomers, membranes, textile finishes and coatings) owe their important properties to the presence of fluorine atoms within their structures. Trifluoromethyl (CF3), trifluoromethylthio (SCF3), and trifluoromethylseleno (SeCF3) groups are among the most popular fluorine-containing functional groups in medicinal chemistry, since the presence of these groups considerably improve pharmacological activities of the molecule due to their high lipophilicity and electronegativity. Recent chemical approaches for the incorporation of the titled groups into organic molecules, based upon direct trifluoromethyl(thiol/selenol)ation of C-H bonds without pre-functionalization of the starting materials. In this context, many new strategies have been developed for oxidative trifluoromethyl(thiol/selenol) ation of terminal alkynes, which allow highly atom economical and rapid access to the biologically and synthetically important trifluoromethyl alkynes, trifluoromethylthioalkynes, and trifluoromethylselenoalkynes. This review intends to summarize the recent advances and developments regarding the direct trifluoromethyl(thiol/selenol)ation of terminal alkynes with particular emphasis on the mechanistic aspects of the reactions which may serve as an inspiration for further research in this appealing research field.

Automated summary

This review summarizes recent advances and developments in the direct introduction of fluorine atoms and fluorine-containing functional groups into organic molecules, with a focus on the mechanistic aspects of these reactions, which may serve as inspiration for further research in this field.