Gold-catalyzed fluorination of alkynes/allenes: mechanistic explanations and reaction scope

Abstract

Since the beginning of this century, there has been a great deal of research on homogeneous gold-catalyzed alkyne fluorination due to the precious values of fluorinated scaffolds in many bioactive natural products, drugs, and agrochemicals. This area of research, which originally took advantage of gold's mild Lewis acidity and tendency to form π-complexes with alkynes, has gained new momentum after Sadighi's discovery in 2007 of Au-catalyzed hydrofluorination of internal alkynes. The methods have enabled direct access to valuable fluoroalkanes, fluoroalkenes, α-fluorocarbonyls, and fluorinated carbo- and hetero-cycles in one pot from readily available alkyne precursors. Both nucleophilic and electrophilic fluorination modes with versatile reactivity have been used to achieve several new cascade reactions. This study covers the literature reports published since 2007 and provides a comprehensive summary of the methods, applications, and mechanistic insights into gold-catalyzed alkyne fluorination using electrophilic and nucleophilic fluorinating reagents.