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One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2016 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 31, 8928-8932 p.Article in journal (Refereed) Published
Abstract [en]

A transition-metal-free, mild, and highly regioselective synthesis of nitroarenes from arenes has been developed. The products are obtained in a sequential one-pot reaction by nitration of iodine(III) reagents with two carbon ligands, which are formed in situ from iodine(I). This novel concept has been extended to formation of aryl azides, and constitutes an important step towards catalytic reactions with these hypervalent iodine reagents. An efficient nitration of isolated diaryl-iodonium salts has also been developed, and the mechanism is proposed to proceed by a [2,2] ligand coupling pathway.

Place, publisher, year, edition, pages
2016. Vol. 55, no 31, 8928-8932 p.
Keyword [en]
arylation, density functional calculations, hypervalent compounds, oxidation, reaction mechanisms
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-135133DOI: 10.1002/anie.201603175ISI: 000383253700022PubMedID: 27272891OAI: oai:DiVA.org:su-135133DiVA: diva2:1044040
Funder
Swedish Research Council
Available from: 2016-11-01 Created: 2016-10-31 Last updated: 2017-06-18Bibliographically approved

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