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Site Selective Nucleophilic Aromatic Substitutions of Azole-Ligated Diaryliodonium Salts

24 August 2022, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Diaryliodonium salts are established electrophilic arylation reagents both in transition metal-catalyzed and transition metal-free reaction methods. Herein we present the application of azole-stabilized diaryliodonium salts with additional thiophen-2-yl-ligands as substrates for metal-free nucleophilic arylations. Besides their synthesis, we demonstrate their application in chemoselective nitrations, oxygenations, aminations as well as thiolations under umpolung conditions. Convenient one-pot procedures that are based on their in situ formation are also discussed

Keywords

Hypervalent Iodine
Iodonium Salts
CH-Activation
Heterocycles

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Version History

Aug 24, 2022 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-qmknd
D O I: 10.26434/chemrxiv-2022-qmknd [opens in a new tab]

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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