Cargando…
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...
Autores principales: | , , , , , , |
---|---|
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 |
_version_ | 1785086060935512064 |
---|---|
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. |
format | Online Article Text |
id | pubmed-10407877 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT gallegogamoalbert siteselectiveandmetalfreechphosphonationofarenesviaphotoactivationofthianthreniumsalts AT reyesmesadavid siteselectiveandmetalfreechphosphonationofarenesviaphotoactivationofthianthreniumsalts AT guinartguillemaxel siteselectiveandmetalfreechphosphonationofarenesviaphotoactivationofthianthreniumsalts AT pleixatsroser siteselectiveandmetalfreechphosphonationofarenesviaphotoactivationofthianthreniumsalts AT gimbertsurinachcarolina siteselectiveandmetalfreechphosphonationofarenesviaphotoactivationofthianthreniumsalts AT vallriberaadelina siteselectiveandmetalfreechphosphonationofarenesviaphotoactivationofthianthreniumsalts AT granadosalbert siteselectiveandmetalfreechphosphonationofarenesviaphotoactivationofthianthreniumsalts |