Efficient deprotection of F-BODIPY derivatives: removal of BF(2) using Brønsted acids

The effective and efficient removal of the BF(2) moiety from F-BODIPY derivatives has been achieved using two common Brønsted acids; treatment with trifluoroacetic acid (TFA) or methanolic hydrogen chloride (HCl) followed by work-up with Ambersep(®) 900 resin (hydroxide form) effects this conversion...

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Detalles Bibliográficos
Autores principales: Yu, Mingfeng, Wong, Joseph K-H, Tang, Cyril, Turner, Peter, Todd, Matthew H, Rutledge, Peter J
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4311716/
https://www.ncbi.nlm.nih.gov/pubmed/25670990
http://dx.doi.org/10.3762/bjoc.11.6
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author Yu, Mingfeng
Wong, Joseph K-H
Tang, Cyril
Turner, Peter
Todd, Matthew H
Rutledge, Peter J
author_facet Yu, Mingfeng
Wong, Joseph K-H
Tang, Cyril
Turner, Peter
Todd, Matthew H
Rutledge, Peter J
author_sort Yu, Mingfeng
collection PubMed
description The effective and efficient removal of the BF(2) moiety from F-BODIPY derivatives has been achieved using two common Brønsted acids; treatment with trifluoroacetic acid (TFA) or methanolic hydrogen chloride (HCl) followed by work-up with Ambersep(®) 900 resin (hydroxide form) effects this conversion in near-quantitative yields. Compared to existing methods, these conditions are relatively mild and operationally simple, requiring only reaction at room temperature for six hours (TFA) or overnight (HCl).
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spelling pubmed-43117162015-02-10 Efficient deprotection of F-BODIPY derivatives: removal of BF(2) using Brønsted acids Yu, Mingfeng Wong, Joseph K-H Tang, Cyril Turner, Peter Todd, Matthew H Rutledge, Peter J Beilstein J Org Chem Letter The effective and efficient removal of the BF(2) moiety from F-BODIPY derivatives has been achieved using two common Brønsted acids; treatment with trifluoroacetic acid (TFA) or methanolic hydrogen chloride (HCl) followed by work-up with Ambersep(®) 900 resin (hydroxide form) effects this conversion in near-quantitative yields. Compared to existing methods, these conditions are relatively mild and operationally simple, requiring only reaction at room temperature for six hours (TFA) or overnight (HCl). Beilstein-Institut 2015-01-09 /pmc/articles/PMC4311716/ /pubmed/25670990 http://dx.doi.org/10.3762/bjoc.11.6 Text en Copyright © 2015, Yu et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Yu, Mingfeng
Wong, Joseph K-H
Tang, Cyril
Turner, Peter
Todd, Matthew H
Rutledge, Peter J
Efficient deprotection of F-BODIPY derivatives: removal of BF(2) using Brønsted acids
title Efficient deprotection of F-BODIPY derivatives: removal of BF(2) using Brønsted acids
title_full Efficient deprotection of F-BODIPY derivatives: removal of BF(2) using Brønsted acids
title_fullStr Efficient deprotection of F-BODIPY derivatives: removal of BF(2) using Brønsted acids
title_full_unstemmed Efficient deprotection of F-BODIPY derivatives: removal of BF(2) using Brønsted acids
title_short Efficient deprotection of F-BODIPY derivatives: removal of BF(2) using Brønsted acids
title_sort efficient deprotection of f-bodipy derivatives: removal of bf(2) using brønsted acids
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4311716/
https://www.ncbi.nlm.nih.gov/pubmed/25670990
http://dx.doi.org/10.3762/bjoc.11.6
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