C–P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds

Simon Oßwald; Christoph Zippel; Zahid Hassan; Martin Nieger; Stefan Bräse

doi:10.1039/D2RA00094F

C–P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds†

Simon Oßwald,

‡^a Christoph Zippel,

‡^a Zahid Hassan,

*^a Martin Nieger^b and Stefan Bräse

*^ac

Author affiliations

* Corresponding authors

^a Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
E-mail: zahid.hassan@kit.edu, braese@kit.edu

^b Department of Chemistry, University of Helsinki, P.O. Box 55, Helsinki, Finland

^c Institute of Biological and Chemical Systems–Functional Molecular Systems, Karlsruhe Institute of Technology (KIT), Herman-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany

Abstract

A new versatile method for the C–P bond formation of (hetero)aryl halides with trimethyl phosphite via a UV-induced photo-Arbuzov reaction, accessing diverse phosphonate-grafted arenes, heteroarenes and co-facially stacked cyclophanes under mild reaction conditions without the need for catalyst, additives, or base is developed. The UV-induced photo-Arbuzov protocol has a wide synthetic scope with large functional group compatibility exemplified by over 30 derivatives. Besides mono-phosphonates, di- and tri-phosphonates are accessible in good to excellent yields. Mild and transition metal-free reaction conditions consolidate this method's potential for synthesizing pharmaceutically relevant compounds and precursors of supramolecular nanostructured materials.

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DOI: https://doi.org/10.1039/D2RA00094F
Article type: Paper
Submitted: 06 Jan 2022
Accepted: 17 Jan 2022
First published: 25 Jan 2022
This article is Open Access

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RSC Adv., 2022,12, 3309-3312

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C–P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds

S. Oßwald, C. Zippel, Z. Hassan, M. Nieger and S. Bräse, RSC Adv., 2022, 12, 3309 DOI: 10.1039/D2RA00094F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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C–P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds†

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C–P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds

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