Visible-light synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones via doubly decarboxylative Giese reaction

Doubly decarboxylative, photoredox synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones is described. The reaction involves two independent decarboxylation processes: the first one initiating the cycle and the second completing the process. Visible light, photoredox catalyst, b...

Descripción completa

Detalles Bibliográficos
Autores principales: Moczulski, Marek, Kowalska, Ewelina, Kuśmierek, Elżbieta, Albrecht, Łukasz, Albrecht, Anna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9037851/
https://www.ncbi.nlm.nih.gov/pubmed/35480728
http://dx.doi.org/10.1039/d1ra05914a
_version_ 1784693806846705664
author Moczulski, Marek
Kowalska, Ewelina
Kuśmierek, Elżbieta
Albrecht, Łukasz
Albrecht, Anna
author_facet Moczulski, Marek
Kowalska, Ewelina
Kuśmierek, Elżbieta
Albrecht, Łukasz
Albrecht, Anna
author_sort Moczulski, Marek
collection PubMed
description Doubly decarboxylative, photoredox synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones is described. The reaction involves two independent decarboxylation processes: the first one initiating the cycle and the second completing the process. Visible light, photoredox catalyst, base, anhydrous solvent and inert atmosphere constitute the key parameters for the success of the developed transformation. The protocol proved applicable for coumarin-3-carboxylic acids and chromone-3-carboxylic acids as well as N-(acyloxy)phthalimide which served as precursors of the corresponding alkyl radicals.
format Online
Article
Text
id pubmed-9037851
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90378512022-04-26 Visible-light synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones via doubly decarboxylative Giese reaction Moczulski, Marek Kowalska, Ewelina Kuśmierek, Elżbieta Albrecht, Łukasz Albrecht, Anna RSC Adv Chemistry Doubly decarboxylative, photoredox synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones is described. The reaction involves two independent decarboxylation processes: the first one initiating the cycle and the second completing the process. Visible light, photoredox catalyst, base, anhydrous solvent and inert atmosphere constitute the key parameters for the success of the developed transformation. The protocol proved applicable for coumarin-3-carboxylic acids and chromone-3-carboxylic acids as well as N-(acyloxy)phthalimide which served as precursors of the corresponding alkyl radicals. The Royal Society of Chemistry 2021-08-16 /pmc/articles/PMC9037851/ /pubmed/35480728 http://dx.doi.org/10.1039/d1ra05914a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Moczulski, Marek
Kowalska, Ewelina
Kuśmierek, Elżbieta
Albrecht, Łukasz
Albrecht, Anna
Visible-light synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones via doubly decarboxylative Giese reaction
title Visible-light synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones via doubly decarboxylative Giese reaction
title_full Visible-light synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones via doubly decarboxylative Giese reaction
title_fullStr Visible-light synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones via doubly decarboxylative Giese reaction
title_full_unstemmed Visible-light synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones via doubly decarboxylative Giese reaction
title_short Visible-light synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones via doubly decarboxylative Giese reaction
title_sort visible-light synthesis of 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones via doubly decarboxylative giese reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9037851/
https://www.ncbi.nlm.nih.gov/pubmed/35480728
http://dx.doi.org/10.1039/d1ra05914a
work_keys_str_mv AT moczulskimarek visiblelightsynthesisof4substitutedchroman2onesand2substitutedchroman4onesviadoublydecarboxylativegiesereaction
AT kowalskaewelina visiblelightsynthesisof4substitutedchroman2onesand2substitutedchroman4onesviadoublydecarboxylativegiesereaction
AT kusmierekelzbieta visiblelightsynthesisof4substitutedchroman2onesand2substitutedchroman4onesviadoublydecarboxylativegiesereaction
AT albrechtłukasz visiblelightsynthesisof4substitutedchroman2onesand2substitutedchroman4onesviadoublydecarboxylativegiesereaction
AT albrechtanna visiblelightsynthesisof4substitutedchroman2onesand2substitutedchroman4onesviadoublydecarboxylativegiesereaction

Ejemplares similares