One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na(2)S(2)O(8)

Various 4-aryl-3-bromocoumarins were smoothly obtained in moderate yields in one pot by treating 3-aryl-2-propynoic acids with diaryliodonium triflates and K(2)CO(3) in the presence of CuCl, followed by the reaction with tetrabutylammonium bromide (TBAB) and Na(2)S(2)O(8). The obtained 3-bromo-4-phe...

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Autores principales: Sasaki, Teppei, Moriyama, Katsuhiko, Togo, Hideo
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/PMC5815302/
https://www.ncbi.nlm.nih.gov/pubmed/29507639
http://dx.doi.org/10.3762/bjoc.14.22
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author Sasaki, Teppei
Moriyama, Katsuhiko
Togo, Hideo
author_facet Sasaki, Teppei
Moriyama, Katsuhiko
Togo, Hideo
author_sort Sasaki, Teppei
collection PubMed
description Various 4-aryl-3-bromocoumarins were smoothly obtained in moderate yields in one pot by treating 3-aryl-2-propynoic acids with diaryliodonium triflates and K(2)CO(3) in the presence of CuCl, followed by the reaction with tetrabutylammonium bromide (TBAB) and Na(2)S(2)O(8). The obtained 3-bromo-4-phenylcoumarin was transformed into 4-phenylcoumarin derivatives bearing C–H, C–S, C–N, and C–C bonds at 3-position.
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spelling pubmed-58153022018-03-05 One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na(2)S(2)O(8) Sasaki, Teppei Moriyama, Katsuhiko Togo, Hideo Beilstein J Org Chem Full Research Paper Various 4-aryl-3-bromocoumarins were smoothly obtained in moderate yields in one pot by treating 3-aryl-2-propynoic acids with diaryliodonium triflates and K(2)CO(3) in the presence of CuCl, followed by the reaction with tetrabutylammonium bromide (TBAB) and Na(2)S(2)O(8). The obtained 3-bromo-4-phenylcoumarin was transformed into 4-phenylcoumarin derivatives bearing C–H, C–S, C–N, and C–C bonds at 3-position. Beilstein-Institut 2018-02-05 /pmc/articles/PMC5815302/ /pubmed/29507639 http://dx.doi.org/10.3762/bjoc.14.22 Text en Copyright © 2018, Sasaki 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
Sasaki, Teppei
Moriyama, Katsuhiko
Togo, Hideo
One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na(2)S(2)O(8)
title One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na(2)S(2)O(8)
title_full One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na(2)S(2)O(8)
title_fullStr One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na(2)S(2)O(8)
title_full_unstemmed One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na(2)S(2)O(8)
title_short One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na(2)S(2)O(8)
title_sort one-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, tbab, and na(2)s(2)o(8)
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5815302/
https://www.ncbi.nlm.nih.gov/pubmed/29507639
http://dx.doi.org/10.3762/bjoc.14.22
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