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

We describe a multi-step continuous-flow procedure for the generation of six-membered diaryliodonium salts. The accompanying scalability and atom economy are significant improvements to existing batch methods. Benzyl acetates are submitted to this two-step procedure as highly available and cheap starting materials. An acid-catalyzed Friedel–Crafts alkylation followed by an anodic oxidative cyclization yielded a defined set of cyclic iodonium salts in a highly substrate-dependent yield.

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>

A multi-step continuous-flow procedure for the generation of six-membered diaryliodonium salts was developed. This is a significant improvement of existing batch methods with regard to scalability and atom economy. The method uses easily accessible benzyl acetates in Friedel-Crafts-like alkylations while a subsequent anodic oxidative cyclization directly generates the corresponding cyclic iodonium salts.

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.