Iodonium Salts as Benzyne Precursors.

Reactions involving benzyne and aryne intermediates have found widespread application in organic synthesis. Various benzyne precursors and benzyne generating procedures are known. Recently, methods of benzyne generation from diaryliodonium salts and related hypervalent iodine compounds have received considerable attention. These methods are characterized by mild reaction conditions and applicability in a broad range of chemical transformations. The present minireview is focused on the preparation and reactivity of hypervalent iodine based benzyne precursors. Furthermore, recent developments in their synthetic application are discussed. Diaryliodonium derivatives can be effectively used for generation of benzyne via decarboxylation, deprotonation, desilylation or deboronation. These reactions are characterized by mild reaction conditions and applicability in a broad range of chemical transformations. In particular, pseudocyclic arylbenziodoxaborole triflates can readily generate aryne intermediates upon treatment with water at room temperature. [ABSTRACT FROM AUTHOR]