Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides

Trisubstituted 5-stibano-1H-1,2,3-triazoles were synthesized in moderate to excellent yields by the Cu-catalyzed [3 + 2] cycloaddition of a ethynylstibane with organic azides in the presence of CuBr (5 mol %) under aerobic conditions. The reaction of 5-stibanotriazole with HCl, I(2), and NOBF(4) aff...

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Autores principales: Yamada, Mizuki, Matsumura, Mio, Uchida, Yuki, Kawahata, Masatoshi, Murata, Yuki, Kakusawa, Naoki, Yamaguchi, Kentaro, Yasuike, Shuji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979910/
https://www.ncbi.nlm.nih.gov/pubmed/27559379
http://dx.doi.org/10.3762/bjoc.12.123
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author Yamada, Mizuki
Matsumura, Mio
Uchida, Yuki
Kawahata, Masatoshi
Murata, Yuki
Kakusawa, Naoki
Yamaguchi, Kentaro
Yasuike, Shuji
author_facet Yamada, Mizuki
Matsumura, Mio
Uchida, Yuki
Kawahata, Masatoshi
Murata, Yuki
Kakusawa, Naoki
Yamaguchi, Kentaro
Yasuike, Shuji
author_sort Yamada, Mizuki
collection PubMed
description Trisubstituted 5-stibano-1H-1,2,3-triazoles were synthesized in moderate to excellent yields by the Cu-catalyzed [3 + 2] cycloaddition of a ethynylstibane with organic azides in the presence of CuBr (5 mol %) under aerobic conditions. The reaction of 5-stibanotriazole with HCl, I(2), and NOBF(4) afforded 1-benzyl-4-phenyltriazole, 1-benzyl-5-iodo-4-phenyltriazole, and a pentavalent organoantimony compound, respectively.
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spelling pubmed-49799102016-08-24 Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides Yamada, Mizuki Matsumura, Mio Uchida, Yuki Kawahata, Masatoshi Murata, Yuki Kakusawa, Naoki Yamaguchi, Kentaro Yasuike, Shuji Beilstein J Org Chem Letter Trisubstituted 5-stibano-1H-1,2,3-triazoles were synthesized in moderate to excellent yields by the Cu-catalyzed [3 + 2] cycloaddition of a ethynylstibane with organic azides in the presence of CuBr (5 mol %) under aerobic conditions. The reaction of 5-stibanotriazole with HCl, I(2), and NOBF(4) afforded 1-benzyl-4-phenyltriazole, 1-benzyl-5-iodo-4-phenyltriazole, and a pentavalent organoantimony compound, respectively. Beilstein-Institut 2016-06-23 /pmc/articles/PMC4979910/ /pubmed/27559379 http://dx.doi.org/10.3762/bjoc.12.123 Text en Copyright © 2016, Yamada 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
Yamada, Mizuki
Matsumura, Mio
Uchida, Yuki
Kawahata, Masatoshi
Murata, Yuki
Kakusawa, Naoki
Yamaguchi, Kentaro
Yasuike, Shuji
Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides
title Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides
title_full Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides
title_fullStr Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides
title_full_unstemmed Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides
title_short Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides
title_sort copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979910/
https://www.ncbi.nlm.nih.gov/pubmed/27559379
http://dx.doi.org/10.3762/bjoc.12.123
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