Two one-pot procedures for the construction of O- and N-bridged diaryliodonium triflates are described. An effective aryne-mediated arylation of o-iodophenols and -sulfonamides provides diarylether and diarylamine intermediates, which are subsequently oxidized and cyclized to the corresponding diaryliodaoxinium and -iodazinium salts. Different derivatizations were applied to demonstrate their capacity as useful building blocks and gain a deeper understanding toward the general reactivity of these underdeveloped but potentially highly useful compounds.

Two one-pot procedures for the construction of carbon-bridged diaryliodonium triflates and tetrafluoroborates are described. Strong Brønsted acids enable the effective Friedel− Crafts alkylation with diversely substituted o-iodobenzyl alcohol derivatives, providing diphenylmethane scaffolds, which are subsequently oxidized and cyclized to the corresponding dibenzo-[b,e]iodininium salts. Based on NMR investigations and density functional theory (DFT) calculations, we could verify the so-farundescribed existence of two stable isomers in cyclic iodonium salts substituted with aliphatic side chains in the carbon bridge. Article pubs.acs.org/joc

In this article we describe an efficient approach for the synthesis of cyclic diaryliodonium salts. The method is based on benzyl alcohols as starting materials and consists of an Friedel-Crafts-arylation/oxidation sequence. Besides a deep optimization, particluar focusing on the choice and ratios of the utilized Bronsted-acids and oxidants, we explore the substrate scope of this transformation. We also discuss an interesting isomerism of cyclic iodonium salts substituted with aliphatic substituents at the bridge head carbon. <br>

Sterically encumbered bis(m‐terphenyl)chalcogenides, (2,6‐Mes2C6H3)2E (E=S, Se, Te) were obtained by the reaction of the chalcogen tetrafluorides, EF4, with three equivalents of m‐terphenyl lithium, 2,6‐Mes2C6H3Li. The single‐electron oxidation of (2,6‐Mes2C6H3)2Te using XeF2/K[B(C6F5)4] afforded the radical cation [(2,6‐Mes2C6H3)2Te][B(C6F5)4] that was isolated and fully characterized. The electrochemical oxidation of the lighter homologs (2,6‐Mes2C6H3)2E (E=S, Se) was irreversible and impaired by rapid decomposition.

Two one-pot procedures for the construction of O- and N-bridged diaryliodonium triflates are described. An effective aryne-mediated arylation of o-iodophenols and sulfonamides provides diarylether and diarylamine intermediates, which are subsequently oxidized and cyclized to the corresponding diaryliodaoxinium and iodazinium salts. Different derivatizations were applied to demonstrate their capacity as useful building blocks and gain a deeper understanding towards the general reactivity of these underdeveloped but potentially highly useful compounds.