Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions

We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone(®) in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acid...

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Autores principales: China, Hideyasu, Kageyama, Nami, Yatabe, Hotaka, Takenaga, Naoko, Dohi, Toshifumi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8036297/
https://www.ncbi.nlm.nih.gov/pubmed/33801611
http://dx.doi.org/10.3390/molecules26071897
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author China, Hideyasu
Kageyama, Nami
Yatabe, Hotaka
Takenaga, Naoko
Dohi, Toshifumi
author_facet China, Hideyasu
Kageyama, Nami
Yatabe, Hotaka
Takenaga, Naoko
Dohi, Toshifumi
author_sort China, Hideyasu
collection PubMed
description We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone(®) in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in excellent yields without contamination by hazardous pentavalent iodine(III) compound.
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spelling pubmed-80362972021-04-12 Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions China, Hideyasu Kageyama, Nami Yatabe, Hotaka Takenaga, Naoko Dohi, Toshifumi Molecules Communication We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone(®) in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in excellent yields without contamination by hazardous pentavalent iodine(III) compound. MDPI 2021-03-27 /pmc/articles/PMC8036297/ /pubmed/33801611 http://dx.doi.org/10.3390/molecules26071897 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 (http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) ).
spellingShingle Communication
China, Hideyasu
Kageyama, Nami
Yatabe, Hotaka
Takenaga, Naoko
Dohi, Toshifumi
Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions
title Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions
title_full Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions
title_fullStr Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions
title_full_unstemmed Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions
title_short Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions
title_sort practical synthesis of 2-iodosobenzoic acid (iba) without contamination by hazardous 2-iodoxybenzoic acid (ibx) under mild conditions
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8036297/
https://www.ncbi.nlm.nih.gov/pubmed/33801611
http://dx.doi.org/10.3390/molecules26071897
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