Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes

The direct C–H functionalization methodology has first been applied to perform transition metal-free C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyllithium. This atom- and step-economical approach, based on one-pot reactions of nucleophilic substitution of hydrogen (S(N)(H)) in non...

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Autores principales: Smyshliaeva, Lidia A, Varaksin, Mikhail V, Slepukhin, Pavel A, Chupakhin, Oleg N, Charushin, Valery N
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6204773/
https://www.ncbi.nlm.nih.gov/pubmed/30410624
http://dx.doi.org/10.3762/bjoc.14.240
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author Smyshliaeva, Lidia A
Varaksin, Mikhail V
Slepukhin, Pavel A
Chupakhin, Oleg N
Charushin, Valery N
author_facet Smyshliaeva, Lidia A
Varaksin, Mikhail V
Slepukhin, Pavel A
Chupakhin, Oleg N
Charushin, Valery N
author_sort Smyshliaeva, Lidia A
collection PubMed
description The direct C–H functionalization methodology has first been applied to perform transition metal-free C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyllithium. This atom- and step-economical approach, based on one-pot reactions of nucleophilic substitution of hydrogen (S(N)(H)) in non-aromatic azaheterocycles, affords novel imidazolyl-modified carboranes of two types (N-oxides and their deoxygenative analogues), which are particularly of interest in the design of advanced materials.
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spelling pubmed-62047732018-11-08 Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes Smyshliaeva, Lidia A Varaksin, Mikhail V Slepukhin, Pavel A Chupakhin, Oleg N Charushin, Valery N Beilstein J Org Chem Letter The direct C–H functionalization methodology has first been applied to perform transition metal-free C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyllithium. This atom- and step-economical approach, based on one-pot reactions of nucleophilic substitution of hydrogen (S(N)(H)) in non-aromatic azaheterocycles, affords novel imidazolyl-modified carboranes of two types (N-oxides and their deoxygenative analogues), which are particularly of interest in the design of advanced materials. Beilstein-Institut 2018-10-12 /pmc/articles/PMC6204773/ /pubmed/30410624 http://dx.doi.org/10.3762/bjoc.14.240 Text en Copyright © 2018, Smyshliaeva 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). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Smyshliaeva, Lidia A
Varaksin, Mikhail V
Slepukhin, Pavel A
Chupakhin, Oleg N
Charushin, Valery N
Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes
title Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes
title_full Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes
title_fullStr Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes
title_full_unstemmed Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes
title_short Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes
title_sort transition metal-free oxidative and deoxygenative c–h/c–li cross-couplings of 2h-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6204773/
https://www.ncbi.nlm.nih.gov/pubmed/30410624
http://dx.doi.org/10.3762/bjoc.14.240
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