A Cobalt Mediated Nitrene Transfer aza-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds

[Image: see text] A cobalt(II) mediated three-component synthesis of 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imines using sulfonyl azides, N-isocyaniminotriphenylphosphorane (NIITP), and carboxylic acids has been developed. This one-pot tandem reaction starts with a nitrene transfer to NIITP,...

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Autores principales: Verdoorn, Daniël S., Ranjan, Prabhat, de Reuver, Tim, Janssen, Elwin, Vande Velde, Christophe M. L., Saya, Jordy M., Maes, Bert U. W., Orru, Romano V. A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10262268/
https://www.ncbi.nlm.nih.gov/pubmed/37224106
http://dx.doi.org/10.1021/acs.orglett.3c00959
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author Verdoorn, Daniël S.
Ranjan, Prabhat
de Reuver, Tim
Janssen, Elwin
Vande Velde, Christophe M. L.
Saya, Jordy M.
Maes, Bert U. W.
Orru, Romano V. A.
author_facet Verdoorn, Daniël S.
Ranjan, Prabhat
de Reuver, Tim
Janssen, Elwin
Vande Velde, Christophe M. L.
Saya, Jordy M.
Maes, Bert U. W.
Orru, Romano V. A.
author_sort Verdoorn, Daniël S.
collection PubMed
description [Image: see text] A cobalt(II) mediated three-component synthesis of 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imines using sulfonyl azides, N-isocyaniminotriphenylphosphorane (NIITP), and carboxylic acids has been developed. This one-pot tandem reaction starts with a nitrene transfer to NIITP, followed by addition of the carboxylic acid to the in situ formed carbodiimide and subsequent intramolecular aza-Wittig reaction. Both the steric constraints of carboxylic acid and the stoichiometry of the employed cobalt salt determine the selectivity toward the two products, i.e. 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imine versus 5-substituted-4-tosyl-2,4-dihydro-3H-1,2,4-triazol-3-one.
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spelling pubmed-102622682023-06-15 A Cobalt Mediated Nitrene Transfer aza-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds Verdoorn, Daniël S. Ranjan, Prabhat de Reuver, Tim Janssen, Elwin Vande Velde, Christophe M. L. Saya, Jordy M. Maes, Bert U. W. Orru, Romano V. A. Org Lett [Image: see text] A cobalt(II) mediated three-component synthesis of 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imines using sulfonyl azides, N-isocyaniminotriphenylphosphorane (NIITP), and carboxylic acids has been developed. This one-pot tandem reaction starts with a nitrene transfer to NIITP, followed by addition of the carboxylic acid to the in situ formed carbodiimide and subsequent intramolecular aza-Wittig reaction. Both the steric constraints of carboxylic acid and the stoichiometry of the employed cobalt salt determine the selectivity toward the two products, i.e. 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2(3H)-imine versus 5-substituted-4-tosyl-2,4-dihydro-3H-1,2,4-triazol-3-one. American Chemical Society 2023-05-24 /pmc/articles/PMC10262268/ /pubmed/37224106 http://dx.doi.org/10.1021/acs.orglett.3c00959 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Verdoorn, Daniël S.
Ranjan, Prabhat
de Reuver, Tim
Janssen, Elwin
Vande Velde, Christophe M. L.
Saya, Jordy M.
Maes, Bert U. W.
Orru, Romano V. A.
A Cobalt Mediated Nitrene Transfer aza-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds
title A Cobalt Mediated Nitrene Transfer aza-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds
title_full A Cobalt Mediated Nitrene Transfer aza-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds
title_fullStr A Cobalt Mediated Nitrene Transfer aza-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds
title_full_unstemmed A Cobalt Mediated Nitrene Transfer aza-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds
title_short A Cobalt Mediated Nitrene Transfer aza-Wittig Cascade Reaction To Access 1,3,4-Oxadiazole Scaffolds
title_sort cobalt mediated nitrene transfer aza-wittig cascade reaction to access 1,3,4-oxadiazole scaffolds
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10262268/
https://www.ncbi.nlm.nih.gov/pubmed/37224106
http://dx.doi.org/10.1021/acs.orglett.3c00959
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