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

Nadezhda M. Metalnikova; Nikita S. Antonkin; Tuan K. Nguyen; Natalia S. Soldatova; Alexander V. Nyuchev; Mikhail A. Kinzhalov; Pavel S. Postnikov

doi:10.3762/bxiv.2025.24.v1

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

Nadezhda M. Metalnikova ,
Nikita S. Antonkin ,
Tuan K. Nguyen ,
Natalia S. Soldatova ,
Alexander V. Nyuchev ,
Mikhail A. Kinzhalov and
Pavel S. Postnikov

Submitting author affiliation:

Tomsk Polytechnic University, Tomsk, Russian Federation

Beilstein Arch. 2025, 202524. https://doi.org/10.3762/bxiv.2025.24.v1

Published 16 Apr 2025

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Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry 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

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.

Keywords: Diaryliodonium salts; isonitriles; arylation; benzamides; photoredox

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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

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)