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Structural Requirements of 1-(2-Pyridinyl)-5-pyrazolones for Disproportionation of Boronic Acids

We observed an unusual formation of four-coordinate boron(III) complexes from the reaction of 1-(2-pyridinyl)-5-pyrazolone derivatives with arylboronic acids in the basic media. The exact mechanism is not clear; however, the use of unprotected boronic acid and the presence of a bidentate ligand appe...

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Autores principales: Cho, Joungmo, Sadu, Venkata Subbaiah, Han, Yohan, Bae, Yunsoo, Lee, Hwajeong, Lee, Kee-In
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8623043/
https://www.ncbi.nlm.nih.gov/pubmed/34833904
http://dx.doi.org/10.3390/molecules26226814
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author Cho, Joungmo
Sadu, Venkata Subbaiah
Han, Yohan
Bae, Yunsoo
Lee, Hwajeong
Lee, Kee-In
author_facet Cho, Joungmo
Sadu, Venkata Subbaiah
Han, Yohan
Bae, Yunsoo
Lee, Hwajeong
Lee, Kee-In
author_sort Cho, Joungmo
collection PubMed
description We observed an unusual formation of four-coordinate boron(III) complexes from the reaction of 1-(2-pyridinyl)-5-pyrazolone derivatives with arylboronic acids in the basic media. The exact mechanism is not clear; however, the use of unprotected boronic acid and the presence of a bidentate ligand appeared to be the key structural requirements for the transformation. The results suggest that base-promoted disproportionation of arylboronic acid with the assistance of the [N,O]-bidentate ligation of 1-(2-pyridinyl)-5-pyrazolone should take place and facilitate the formation of pyrazole diarylborinate. Experiments to obtain a deeper understanding of its mechanism are currently underway.
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spelling pubmed-86230432021-11-27 Structural Requirements of 1-(2-Pyridinyl)-5-pyrazolones for Disproportionation of Boronic Acids Cho, Joungmo Sadu, Venkata Subbaiah Han, Yohan Bae, Yunsoo Lee, Hwajeong Lee, Kee-In Molecules Article We observed an unusual formation of four-coordinate boron(III) complexes from the reaction of 1-(2-pyridinyl)-5-pyrazolone derivatives with arylboronic acids in the basic media. The exact mechanism is not clear; however, the use of unprotected boronic acid and the presence of a bidentate ligand appeared to be the key structural requirements for the transformation. The results suggest that base-promoted disproportionation of arylboronic acid with the assistance of the [N,O]-bidentate ligation of 1-(2-pyridinyl)-5-pyrazolone should take place and facilitate the formation of pyrazole diarylborinate. Experiments to obtain a deeper understanding of its mechanism are currently underway. MDPI 2021-11-11 /pmc/articles/PMC8623043/ /pubmed/34833904 http://dx.doi.org/10.3390/molecules26226814 Text en © 2021 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
Cho, Joungmo
Sadu, Venkata Subbaiah
Han, Yohan
Bae, Yunsoo
Lee, Hwajeong
Lee, Kee-In
Structural Requirements of 1-(2-Pyridinyl)-5-pyrazolones for Disproportionation of Boronic Acids
title Structural Requirements of 1-(2-Pyridinyl)-5-pyrazolones for Disproportionation of Boronic Acids
title_full Structural Requirements of 1-(2-Pyridinyl)-5-pyrazolones for Disproportionation of Boronic Acids
title_fullStr Structural Requirements of 1-(2-Pyridinyl)-5-pyrazolones for Disproportionation of Boronic Acids
title_full_unstemmed Structural Requirements of 1-(2-Pyridinyl)-5-pyrazolones for Disproportionation of Boronic Acids
title_short Structural Requirements of 1-(2-Pyridinyl)-5-pyrazolones for Disproportionation of Boronic Acids
title_sort structural requirements of 1-(2-pyridinyl)-5-pyrazolones for disproportionation of boronic acids
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8623043/
https://www.ncbi.nlm.nih.gov/pubmed/34833904
http://dx.doi.org/10.3390/molecules26226814
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