One-Pot Synthesis and Conformational Analysis of Six-Membered Cyclic Iodonium Salts

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 ar...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-07, Vol.85 (14), p.9161-9178
Main Authors: Caspers, Lucien D, Spils, Julian, Damrath, Mattis, Lork, Enno, Nachtsheim, Boris J
Format: Article
Language:English
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Summary: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-far-undescribed existence of two stable isomers in cyclic iodonium salts substituted with aliphatic side chains in the carbon bridge.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01125