Photocatalyzed Arylation of Isonitriles by Diaryliodonium Salts towards N-Substituted Benzamides

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The paper studies a photoredox method for arylating isonitriles using diaryliodonium salts to synthesize a broad range of N-substituted arylamides, including benzamides, under mild conditions. Using symmetric and unsymmetric iodonium salts, the authors report that the approach enables aryl transfer to form the desired amide products, and they investigate a plausible reaction mechanism and the selectivity of aryl transfer for the asymmetric case. A stated caveat is that the work is presented as a preprint, with the peer-reviewed version separately linked as Beilstein Journal of Organic Chemistry (BJOC 21(110)), rather than being fully established solely as peer-reviewed text in the provided content. The paper does not explicitly discuss endometriosis or adenomyosis; it was included in the corpus via a keyword match in the upstream search index.

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Abstract

The arylation of isonitriles by diaryliodonium salts under photoredox conditions has been proposed for the first time. The suggested procedure allows preparing the broad range of N-substituted arylamides using both symmetric and unsymmetric diaryliodonium salts in mild conditions. The plausible mechanism for the reaction and the selectivity of aryl transfer in case of asymmetrical iodonium salts was studied.
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Materials

chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry The arylation of isonitriles by diaryliodonium salts under photoredox conditions has been proposed for the first time. The suggested procedure allows preparing the broad range of N-substituted arylamides using both symmetric and unsymmetric diaryliodonium salts in mild conditions. The plausible mechanism for the reaction and the selectivity of aryl transfer in case of asymmetrical iodonium salts was studied.

Keywords

Diaryliodonium salts; isonitriles; arylation; benzamides; photoredox | Format: PDF | Size: 8.2 MB | Download | When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information: Metalnikova, N. M.; Antonkin, N. S.; Nguyen, T. K.; Soldatova, N. S.; Nyuchev, A. V.; Kinzhalov, M. A.; Postnikov, P. S. Beilstein Arch. 2025, 202524. doi:10.3762/bxiv.2025.24.v1 Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below. Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero. © 2025 Metalnikova et al.; licensee Beilstein-Institut. This is an open access work licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-archives.org/xiv/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this work could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.

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