An air-stable bisboron complex: a practical bidentate Lewis acid catalyst

We report an air-stable bisboron complex as an efficient catalyst for the inverse electron-demand Diels–Alder (IEDDA) reaction of 1,2-diazine as well as 1,2,4,5-tetrazine. Its stability towards air and moisture was demonstrated by NMR studies enabling its application in organic transformations witho...

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Autores principales: Hong, Longcheng, Ahles, Sebastian, Heindl, Andreas H, Tiétcha, Gastelle, Petrov, Andrey, Lu, Zhenpin, Logemann, Christian, Wegner, Hermann A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5870160/
https://www.ncbi.nlm.nih.gov/pubmed/29623123
http://dx.doi.org/10.3762/bjoc.14.48
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author Hong, Longcheng
Ahles, Sebastian
Heindl, Andreas H
Tiétcha, Gastelle
Petrov, Andrey
Lu, Zhenpin
Logemann, Christian
Wegner, Hermann A
author_facet Hong, Longcheng
Ahles, Sebastian
Heindl, Andreas H
Tiétcha, Gastelle
Petrov, Andrey
Lu, Zhenpin
Logemann, Christian
Wegner, Hermann A
author_sort Hong, Longcheng
collection PubMed
description We report an air-stable bisboron complex as an efficient catalyst for the inverse electron-demand Diels–Alder (IEDDA) reaction of 1,2-diazine as well as 1,2,4,5-tetrazine. Its stability towards air and moisture was demonstrated by NMR studies enabling its application in organic transformations without glovebox. A one-pot procedure for its synthesis was developed starting from 1,2-bis(trimethylsilyl)benzene greatly enhancing its practicality. Comparative reactions were carried out to evaluate its catalytic activity in IEDDA reactions of diazine including phthalazine as well as 1,2,4,5-tetrazine.
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spelling pubmed-58701602018-04-05 An air-stable bisboron complex: a practical bidentate Lewis acid catalyst Hong, Longcheng Ahles, Sebastian Heindl, Andreas H Tiétcha, Gastelle Petrov, Andrey Lu, Zhenpin Logemann, Christian Wegner, Hermann A Beilstein J Org Chem Full Research Paper We report an air-stable bisboron complex as an efficient catalyst for the inverse electron-demand Diels–Alder (IEDDA) reaction of 1,2-diazine as well as 1,2,4,5-tetrazine. Its stability towards air and moisture was demonstrated by NMR studies enabling its application in organic transformations without glovebox. A one-pot procedure for its synthesis was developed starting from 1,2-bis(trimethylsilyl)benzene greatly enhancing its practicality. Comparative reactions were carried out to evaluate its catalytic activity in IEDDA reactions of diazine including phthalazine as well as 1,2,4,5-tetrazine. Beilstein-Institut 2018-03-13 /pmc/articles/PMC5870160/ /pubmed/29623123 http://dx.doi.org/10.3762/bjoc.14.48 Text en Copyright © 2018, Hong et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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 Full Research Paper
Hong, Longcheng
Ahles, Sebastian
Heindl, Andreas H
Tiétcha, Gastelle
Petrov, Andrey
Lu, Zhenpin
Logemann, Christian
Wegner, Hermann A
An air-stable bisboron complex: a practical bidentate Lewis acid catalyst
title An air-stable bisboron complex: a practical bidentate Lewis acid catalyst
title_full An air-stable bisboron complex: a practical bidentate Lewis acid catalyst
title_fullStr An air-stable bisboron complex: a practical bidentate Lewis acid catalyst
title_full_unstemmed An air-stable bisboron complex: a practical bidentate Lewis acid catalyst
title_short An air-stable bisboron complex: a practical bidentate Lewis acid catalyst
title_sort air-stable bisboron complex: a practical bidentate lewis acid catalyst
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5870160/
https://www.ncbi.nlm.nih.gov/pubmed/29623123
http://dx.doi.org/10.3762/bjoc.14.48
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