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Synthesis of 2-Cyanobenzothiazoles via Pd-Catalyzed/Cu-Assisted C-H Functionalization/Intramolecular C-S Bond Formation from N-Arylcyanothioformamides †

We report herein on a catalytic system involving palladium and copper to achieve the cyclization of N-arylcyanothioformamides and the synthesis of 2-cyanobenzothiazoles. The C-H functionalization/intramolecular C-S bond formation reaction was achieved in the presence of air, using 2.0 equiv of an in...

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Autores principales: Broudic, Nathan, Pacheco-Benichou, Alexandra, Fruit, Corinne, Besson, Thierry
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9738468/
https://www.ncbi.nlm.nih.gov/pubmed/36500519
http://dx.doi.org/10.3390/molecules27238426
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author Broudic, Nathan
Pacheco-Benichou, Alexandra
Fruit, Corinne
Besson, Thierry
author_facet Broudic, Nathan
Pacheco-Benichou, Alexandra
Fruit, Corinne
Besson, Thierry
author_sort Broudic, Nathan
collection PubMed
description We report herein on a catalytic system involving palladium and copper to achieve the cyclization of N-arylcyanothioformamides and the synthesis of 2-cyanobenzothiazoles. The C-H functionalization/intramolecular C-S bond formation reaction was achieved in the presence of air, using 2.0 equiv of an inorganic additive (KI). In many cases, the reaction led to a sole product regioselectively obtained in good yields, allowing the synthesis of a wide range of substituted 2-cyanobenzothiazole derivatives, providing valuable building blocks for the design of more complex heterocyclic or molecular labeling systems.
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spelling pubmed-97384682022-12-11 Synthesis of 2-Cyanobenzothiazoles via Pd-Catalyzed/Cu-Assisted C-H Functionalization/Intramolecular C-S Bond Formation from N-Arylcyanothioformamides † Broudic, Nathan Pacheco-Benichou, Alexandra Fruit, Corinne Besson, Thierry Molecules Article We report herein on a catalytic system involving palladium and copper to achieve the cyclization of N-arylcyanothioformamides and the synthesis of 2-cyanobenzothiazoles. The C-H functionalization/intramolecular C-S bond formation reaction was achieved in the presence of air, using 2.0 equiv of an inorganic additive (KI). In many cases, the reaction led to a sole product regioselectively obtained in good yields, allowing the synthesis of a wide range of substituted 2-cyanobenzothiazole derivatives, providing valuable building blocks for the design of more complex heterocyclic or molecular labeling systems. MDPI 2022-12-01 /pmc/articles/PMC9738468/ /pubmed/36500519 http://dx.doi.org/10.3390/molecules27238426 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Broudic, Nathan
Pacheco-Benichou, Alexandra
Fruit, Corinne
Besson, Thierry
Synthesis of 2-Cyanobenzothiazoles via Pd-Catalyzed/Cu-Assisted C-H Functionalization/Intramolecular C-S Bond Formation from N-Arylcyanothioformamides †
title Synthesis of 2-Cyanobenzothiazoles via Pd-Catalyzed/Cu-Assisted C-H Functionalization/Intramolecular C-S Bond Formation from N-Arylcyanothioformamides †
title_full Synthesis of 2-Cyanobenzothiazoles via Pd-Catalyzed/Cu-Assisted C-H Functionalization/Intramolecular C-S Bond Formation from N-Arylcyanothioformamides †
title_fullStr Synthesis of 2-Cyanobenzothiazoles via Pd-Catalyzed/Cu-Assisted C-H Functionalization/Intramolecular C-S Bond Formation from N-Arylcyanothioformamides †
title_full_unstemmed Synthesis of 2-Cyanobenzothiazoles via Pd-Catalyzed/Cu-Assisted C-H Functionalization/Intramolecular C-S Bond Formation from N-Arylcyanothioformamides †
title_short Synthesis of 2-Cyanobenzothiazoles via Pd-Catalyzed/Cu-Assisted C-H Functionalization/Intramolecular C-S Bond Formation from N-Arylcyanothioformamides †
title_sort synthesis of 2-cyanobenzothiazoles via pd-catalyzed/cu-assisted c-h functionalization/intramolecular c-s bond formation from n-arylcyanothioformamides †
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9738468/
https://www.ncbi.nlm.nih.gov/pubmed/36500519
http://dx.doi.org/10.3390/molecules27238426
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