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Synthesis of C4-alkynylisoxazoles via a Pd-catalyzed Sonogashira cross-coupling reaction

A Pd-catalyzed Sonogashira cross-coupling reaction for the synthesis of C4-alkynylisoxazoles from 3,5-disubsitituted-4-iodoisoxazoles and terminal alkynes was described, which could afford the corresponding products with high yield (up to 98%). The results indicated that the steric effect from the g...

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Detalles Bibliográficos
Autores principales: Yang, Wen, Yao, Yongqi, Yang, Xin, Deng, Yingying, Lin, Qifu, Yang, Dingqiao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9061866/
https://www.ncbi.nlm.nih.gov/pubmed/35517684
http://dx.doi.org/10.1039/c9ra00577c
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author Yang, Wen
Yao, Yongqi
Yang, Xin
Deng, Yingying
Lin, Qifu
Yang, Dingqiao
author_facet Yang, Wen
Yao, Yongqi
Yang, Xin
Deng, Yingying
Lin, Qifu
Yang, Dingqiao
author_sort Yang, Wen
collection PubMed
description A Pd-catalyzed Sonogashira cross-coupling reaction for the synthesis of C4-alkynylisoxazoles from 3,5-disubsitituted-4-iodoisoxazoles and terminal alkynes was described, which could afford the corresponding products with high yield (up to 98%). The results indicated that the steric effect from the group at the C3 position of the isoxazole had greater influence on the cross-coupling reaction than that from the group at the C5 position. In addition, the group at the C3 position of the isoxazole showed negligible electronic effects on the cross-coupling reaction. Furthermore, a gram-scale reaction of the Sonogashira coupling reaction was also investigated. Finally, a plausible mechanism for the Sonogashira coupling reaction was proposed.
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spelling pubmed-90618662022-05-04 Synthesis of C4-alkynylisoxazoles via a Pd-catalyzed Sonogashira cross-coupling reaction Yang, Wen Yao, Yongqi Yang, Xin Deng, Yingying Lin, Qifu Yang, Dingqiao RSC Adv Chemistry A Pd-catalyzed Sonogashira cross-coupling reaction for the synthesis of C4-alkynylisoxazoles from 3,5-disubsitituted-4-iodoisoxazoles and terminal alkynes was described, which could afford the corresponding products with high yield (up to 98%). The results indicated that the steric effect from the group at the C3 position of the isoxazole had greater influence on the cross-coupling reaction than that from the group at the C5 position. In addition, the group at the C3 position of the isoxazole showed negligible electronic effects on the cross-coupling reaction. Furthermore, a gram-scale reaction of the Sonogashira coupling reaction was also investigated. Finally, a plausible mechanism for the Sonogashira coupling reaction was proposed. The Royal Society of Chemistry 2019-03-18 /pmc/articles/PMC9061866/ /pubmed/35517684 http://dx.doi.org/10.1039/c9ra00577c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Yang, Wen
Yao, Yongqi
Yang, Xin
Deng, Yingying
Lin, Qifu
Yang, Dingqiao
Synthesis of C4-alkynylisoxazoles via a Pd-catalyzed Sonogashira cross-coupling reaction
title Synthesis of C4-alkynylisoxazoles via a Pd-catalyzed Sonogashira cross-coupling reaction
title_full Synthesis of C4-alkynylisoxazoles via a Pd-catalyzed Sonogashira cross-coupling reaction
title_fullStr Synthesis of C4-alkynylisoxazoles via a Pd-catalyzed Sonogashira cross-coupling reaction
title_full_unstemmed Synthesis of C4-alkynylisoxazoles via a Pd-catalyzed Sonogashira cross-coupling reaction
title_short Synthesis of C4-alkynylisoxazoles via a Pd-catalyzed Sonogashira cross-coupling reaction
title_sort synthesis of c4-alkynylisoxazoles via a pd-catalyzed sonogashira cross-coupling reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9061866/
https://www.ncbi.nlm.nih.gov/pubmed/35517684
http://dx.doi.org/10.1039/c9ra00577c
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