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One-Pot Synthesis and Conformational Analysis of 6-Membered Cyclic Iodonium Salts

preprint
submitted on 02.05.2020 and posted on 05.05.2020 by Lucien Caspers, Julian Spils, Mattis Damrath, Enno Lork, Boris Nachtsheim
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.

History

Email Address of Submitting Author

nachtsheim@uni-bremen.de

Institution

University of Bremen

Country

Germany

ORCID For Submitting Author

0000-0002-3759-2770

Declaration of Conflict of Interest

No conflicts to declare

Version Notes

first version

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