One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation

Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and te...

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Autores principales: Chen, Fa-Jie, Hua, Zhenguo, Chen, Jianhui, Chen, Jiajia, Lee, Daesung, Xia, Yuanzhi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8100659/
https://www.ncbi.nlm.nih.gov/pubmed/33968892
http://dx.doi.org/10.3389/fchem.2020.621545
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author Chen, Fa-Jie
Hua, Zhenguo
Chen, Jianhui
Chen, Jiajia
Lee, Daesung
Xia, Yuanzhi
author_facet Chen, Fa-Jie
Hua, Zhenguo
Chen, Jianhui
Chen, Jiajia
Lee, Daesung
Xia, Yuanzhi
author_sort Chen, Fa-Jie
collection PubMed
description Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-β-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity.
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spelling pubmed-81006592021-05-07 One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation Chen, Fa-Jie Hua, Zhenguo Chen, Jianhui Chen, Jiajia Lee, Daesung Xia, Yuanzhi Front Chem Chemistry Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-β-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity. Frontiers Media S.A. 2021-04-22 /pmc/articles/PMC8100659/ /pubmed/33968892 http://dx.doi.org/10.3389/fchem.2020.621545 Text en Copyright © 2021 Chen, Hua, Chen, Chen, Lee and Xia. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Chen, Fa-Jie
Hua, Zhenguo
Chen, Jianhui
Chen, Jiajia
Lee, Daesung
Xia, Yuanzhi
One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation
title One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation
title_full One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation
title_fullStr One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation
title_full_unstemmed One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation
title_short One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation
title_sort one-pot synthesis of (z)-β-halovinyl ketones via the cascade of sonogashira coupling and hydrohalogenation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8100659/
https://www.ncbi.nlm.nih.gov/pubmed/33968892
http://dx.doi.org/10.3389/fchem.2020.621545
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