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Site-selective and metal-free C–H phosphonation of arenes via photoactivation of thianthrenium salts

Aryl phosphonates are prevalent moieties in medicinal chemistry and agrochemicals. Their chemical synthesis normally relies on the use of precious metals, harsh conditions or aryl halides as substrates. Herein, we describe a sustainable light-promoted and site-selective C–H phosphonation of arenes v...

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Autores principales: Gallego-Gamo, Albert, Reyes-Mesa, David, Guinart-Guillem, Axel, Pleixats, Roser, Gimbert-Suriñach, Carolina, Vallribera, Adelina, Granados, Albert
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10407877/
https://www.ncbi.nlm.nih.gov/pubmed/37559697
http://dx.doi.org/10.1039/d3ra04512a
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author Gallego-Gamo, Albert
Reyes-Mesa, David
Guinart-Guillem, Axel
Pleixats, Roser
Gimbert-Suriñach, Carolina
Vallribera, Adelina
Granados, Albert
author_facet Gallego-Gamo, Albert
Reyes-Mesa, David
Guinart-Guillem, Axel
Pleixats, Roser
Gimbert-Suriñach, Carolina
Vallribera, Adelina
Granados, Albert
author_sort Gallego-Gamo, Albert
collection PubMed
description Aryl phosphonates are prevalent moieties in medicinal chemistry and agrochemicals. Their chemical synthesis normally relies on the use of precious metals, harsh conditions or aryl halides as substrates. Herein, we describe a sustainable light-promoted and site-selective C–H phosphonation of arenes via thianthrenation and the formation of an electron donor–acceptor complex (EDA) as key steps. The method tolerates a wide range of functional groups including biomolecules. The use of sunlight also promotes this transformation and our mechanistic investigations support a radical chain mechanism.
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spelling pubmed-104078772023-08-09 Site-selective and metal-free C–H phosphonation of arenes via photoactivation of thianthrenium salts Gallego-Gamo, Albert Reyes-Mesa, David Guinart-Guillem, Axel Pleixats, Roser Gimbert-Suriñach, Carolina Vallribera, Adelina Granados, Albert RSC Adv Chemistry Aryl phosphonates are prevalent moieties in medicinal chemistry and agrochemicals. Their chemical synthesis normally relies on the use of precious metals, harsh conditions or aryl halides as substrates. Herein, we describe a sustainable light-promoted and site-selective C–H phosphonation of arenes via thianthrenation and the formation of an electron donor–acceptor complex (EDA) as key steps. The method tolerates a wide range of functional groups including biomolecules. The use of sunlight also promotes this transformation and our mechanistic investigations support a radical chain mechanism. The Royal Society of Chemistry 2023-08-08 /pmc/articles/PMC10407877/ /pubmed/37559697 http://dx.doi.org/10.1039/d3ra04512a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Gallego-Gamo, Albert
Reyes-Mesa, David
Guinart-Guillem, Axel
Pleixats, Roser
Gimbert-Suriñach, Carolina
Vallribera, Adelina
Granados, Albert
Site-selective and metal-free C–H phosphonation of arenes via photoactivation of thianthrenium salts
title Site-selective and metal-free C–H phosphonation of arenes via photoactivation of thianthrenium salts
title_full Site-selective and metal-free C–H phosphonation of arenes via photoactivation of thianthrenium salts
title_fullStr Site-selective and metal-free C–H phosphonation of arenes via photoactivation of thianthrenium salts
title_full_unstemmed Site-selective and metal-free C–H phosphonation of arenes via photoactivation of thianthrenium salts
title_short Site-selective and metal-free C–H phosphonation of arenes via photoactivation of thianthrenium salts
title_sort site-selective and metal-free c–h phosphonation of arenes via photoactivation of thianthrenium salts
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10407877/
https://www.ncbi.nlm.nih.gov/pubmed/37559697
http://dx.doi.org/10.1039/d3ra04512a
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