One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines

The Au(III)-catalyzed cyclization of 2-alkynylanilines was combined in a one-pot procedure with the Au(I)-catalyzed C3-selective direct alkynylation of indoles using the benziodoxolone reagent TIPS-EBX to give a mild, easy and straightforward entry to 2-substituted-3-alkynylindoles. The reaction can...

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Detalles Bibliográficos
Autores principales: Brand, Jonathan P, Chevalley, Clara, Waser, Jérôme
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3107533/
https://www.ncbi.nlm.nih.gov/pubmed/21647264
http://dx.doi.org/10.3762/bjoc.7.65
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author Brand, Jonathan P
Chevalley, Clara
Waser, Jérôme
author_facet Brand, Jonathan P
Chevalley, Clara
Waser, Jérôme
author_sort Brand, Jonathan P
collection PubMed
description The Au(III)-catalyzed cyclization of 2-alkynylanilines was combined in a one-pot procedure with the Au(I)-catalyzed C3-selective direct alkynylation of indoles using the benziodoxolone reagent TIPS-EBX to give a mild, easy and straightforward entry to 2-substituted-3-alkynylindoles. The reaction can be applied to unprotected anilines, was tolerant to functional groups and easy to carry out (RT, and requires neither an inert atmosphere nor special solvents).
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spelling pubmed-31075332011-06-06 One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines Brand, Jonathan P Chevalley, Clara Waser, Jérôme Beilstein J Org Chem Letter The Au(III)-catalyzed cyclization of 2-alkynylanilines was combined in a one-pot procedure with the Au(I)-catalyzed C3-selective direct alkynylation of indoles using the benziodoxolone reagent TIPS-EBX to give a mild, easy and straightforward entry to 2-substituted-3-alkynylindoles. The reaction can be applied to unprotected anilines, was tolerant to functional groups and easy to carry out (RT, and requires neither an inert atmosphere nor special solvents). Beilstein-Institut 2011-05-04 /pmc/articles/PMC3107533/ /pubmed/21647264 http://dx.doi.org/10.3762/bjoc.7.65 Text en Copyright © 2011, Brand 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
Brand, Jonathan P
Chevalley, Clara
Waser, Jérôme
One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines
title One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines
title_full One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines
title_fullStr One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines
title_full_unstemmed One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines
title_short One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines
title_sort one-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3107533/
https://www.ncbi.nlm.nih.gov/pubmed/21647264
http://dx.doi.org/10.3762/bjoc.7.65
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