Silver‐Catalyzed Stereoselective Aminosulfonylation of Alkynes

A silver‐catalyzed intermolecular aminosulfonylation of terminal alkynes with sodium sulfinates and TMSN(3) is reported. This three‐component reaction proceeds through sequential hydroazidation of the terminal alkyne and addition of a sulfonyl radical to the resultant vinyl azide. The method enables...

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Autores principales: Ning, Yongquan, Ji, Qinghe, Liao, Peiqiu, Anderson, Edward A., Bi, Xihe
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5655761/
https://www.ncbi.nlm.nih.gov/pubmed/28627090
http://dx.doi.org/10.1002/anie.201705122
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author Ning, Yongquan
Ji, Qinghe
Liao, Peiqiu
Anderson, Edward A.
Bi, Xihe
author_facet Ning, Yongquan
Ji, Qinghe
Liao, Peiqiu
Anderson, Edward A.
Bi, Xihe
author_sort Ning, Yongquan
collection PubMed
description A silver‐catalyzed intermolecular aminosulfonylation of terminal alkynes with sodium sulfinates and TMSN(3) is reported. This three‐component reaction proceeds through sequential hydroazidation of the terminal alkyne and addition of a sulfonyl radical to the resultant vinyl azide. The method enables the stereoselective synthesis of a wide range of β‐sulfonyl enamines without electron‐withdrawing groups on the nitrogen atom. These enamines are found to be suitable for a variety of further transformations.
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spelling pubmed-56557612017-11-01 Silver‐Catalyzed Stereoselective Aminosulfonylation of Alkynes Ning, Yongquan Ji, Qinghe Liao, Peiqiu Anderson, Edward A. Bi, Xihe Angew Chem Int Ed Engl Communications A silver‐catalyzed intermolecular aminosulfonylation of terminal alkynes with sodium sulfinates and TMSN(3) is reported. This three‐component reaction proceeds through sequential hydroazidation of the terminal alkyne and addition of a sulfonyl radical to the resultant vinyl azide. The method enables the stereoselective synthesis of a wide range of β‐sulfonyl enamines without electron‐withdrawing groups on the nitrogen atom. These enamines are found to be suitable for a variety of further transformations. John Wiley and Sons Inc. 2017-07-07 2017-10-23 /pmc/articles/PMC5655761/ /pubmed/28627090 http://dx.doi.org/10.1002/anie.201705122 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Ning, Yongquan
Ji, Qinghe
Liao, Peiqiu
Anderson, Edward A.
Bi, Xihe
Silver‐Catalyzed Stereoselective Aminosulfonylation of Alkynes
title Silver‐Catalyzed Stereoselective Aminosulfonylation of Alkynes
title_full Silver‐Catalyzed Stereoselective Aminosulfonylation of Alkynes
title_fullStr Silver‐Catalyzed Stereoselective Aminosulfonylation of Alkynes
title_full_unstemmed Silver‐Catalyzed Stereoselective Aminosulfonylation of Alkynes
title_short Silver‐Catalyzed Stereoselective Aminosulfonylation of Alkynes
title_sort silver‐catalyzed stereoselective aminosulfonylation of alkynes
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5655761/
https://www.ncbi.nlm.nih.gov/pubmed/28627090
http://dx.doi.org/10.1002/anie.201705122
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AT andersonedwarda silvercatalyzedstereoselectiveaminosulfonylationofalkynes
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