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: Joungmo Cho, Venkata Subbaiah Sadu, Yohan Han, Yunsoo Bae, Hwajeong Lee, Kee-In Lee
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Publicado: MDPI AG 2021
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spelling oai:doaj.org-article:8f6760d80b164164b91d00995d796abe2021-11-25T18:27:26ZStructural Requirements of 1-(2-Pyridinyl)-5-pyrazolones for Disproportionation of Boronic Acids10.3390/molecules262268141420-3049https://doaj.org/article/8f6760d80b164164b91d00995d796abe2021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6814https://doaj.org/toc/1420-3049We 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 [<i>N</i>,<i>O</i>]-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.Joungmo ChoVenkata Subbaiah SaduYohan HanYunsoo BaeHwajeong LeeKee-In LeeMDPI AGarticle1-(2-pyridinyl)-5-pyrazolone[<i>N</i>,<i>O</i>]-bidentate ligandarylboronic acidbasediarylborinationfour-coordinate boron(III) complexOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6814, p 6814 (2021)
institution DOAJ
collection DOAJ
language EN
topic 1-(2-pyridinyl)-5-pyrazolone
[<i>N</i>,<i>O</i>]-bidentate ligand
arylboronic acid
base
diarylborination
four-coordinate boron(III) complex
Organic chemistry
QD241-441
spellingShingle 1-(2-pyridinyl)-5-pyrazolone
[<i>N</i>,<i>O</i>]-bidentate ligand
arylboronic acid
base
diarylborination
four-coordinate boron(III) complex
Organic chemistry
QD241-441
Joungmo Cho
Venkata Subbaiah Sadu
Yohan Han
Yunsoo Bae
Hwajeong Lee
Kee-In Lee
Structural Requirements of 1-(2-Pyridinyl)-5-pyrazolones for Disproportionation of Boronic Acids
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 [<i>N</i>,<i>O</i>]-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.
format article
author Joungmo Cho
Venkata Subbaiah Sadu
Yohan Han
Yunsoo Bae
Hwajeong Lee
Kee-In Lee
author_facet Joungmo Cho
Venkata Subbaiah Sadu
Yohan Han
Yunsoo Bae
Hwajeong Lee
Kee-In Lee
author_sort Joungmo Cho
title 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_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_sort structural requirements of 1-(2-pyridinyl)-5-pyrazolones for disproportionation of boronic acids
publisher MDPI AG
publishDate 2021
url https://doaj.org/article/8f6760d80b164164b91d00995d796abe
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