Cargando…

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

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, add...

Descripción completa

Detalles Bibliográficos
Autores principales: Oßwald, Simon, Zippel, Christoph, Hassan, Zahid, Nieger, Martin, Bräse, Stefan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8979280/
https://www.ncbi.nlm.nih.gov/pubmed/35425357
http://dx.doi.org/10.1039/d2ra00094f
_version_ 1784681142536896512
author Oßwald, Simon
Zippel, Christoph
Hassan, Zahid
Nieger, Martin
Bräse, Stefan
author_facet Oßwald, Simon
Zippel, Christoph
Hassan, Zahid
Nieger, Martin
Bräse, Stefan
author_sort Oßwald, Simon
collection PubMed
description 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.
format Online
Article
Text
id pubmed-8979280
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-89792802022-04-13 C–P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds Oßwald, Simon Zippel, Christoph Hassan, Zahid Nieger, Martin Bräse, Stefan RSC Adv Chemistry 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. The Royal Society of Chemistry 2022-01-25 /pmc/articles/PMC8979280/ /pubmed/35425357 http://dx.doi.org/10.1039/d2ra00094f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Oßwald, Simon
Zippel, Christoph
Hassan, Zahid
Nieger, Martin
Bräse, Stefan
C–P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds
title C–P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds
title_full C–P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds
title_fullStr C–P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds
title_full_unstemmed C–P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds
title_short C–P bond formation of cyclophanyl-, and aryl halides via a UV-induced photo Arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds
title_sort c–p bond formation of cyclophanyl-, and aryl halides via a uv-induced photo arbuzov reaction: a versatile portal to phosphonate-grafted scaffolds
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8979280/
https://www.ncbi.nlm.nih.gov/pubmed/35425357
http://dx.doi.org/10.1039/d2ra00094f
work_keys_str_mv AT oßwaldsimon cpbondformationofcyclophanylandarylhalidesviaauvinducedphotoarbuzovreactionaversatileportaltophosphonategraftedscaffolds
AT zippelchristoph cpbondformationofcyclophanylandarylhalidesviaauvinducedphotoarbuzovreactionaversatileportaltophosphonategraftedscaffolds
AT hassanzahid cpbondformationofcyclophanylandarylhalidesviaauvinducedphotoarbuzovreactionaversatileportaltophosphonategraftedscaffolds
AT niegermartin cpbondformationofcyclophanylandarylhalidesviaauvinducedphotoarbuzovreactionaversatileportaltophosphonategraftedscaffolds
AT brasestefan cpbondformationofcyclophanylandarylhalidesviaauvinducedphotoarbuzovreactionaversatileportaltophosphonategraftedscaffolds