α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction

α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction

In the palladium-catalyzed C−C coupling reaction, electron-rich phosphine ligands and a catalytic amount of catalyst loading are required in most cases. Herein, a bench-stable, easily modified and less toxic alkynone was utilized in palladium-catalyzed Sonogashira coupling to replace conve...

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Main Authors: Meng Guo, Zhen Wei, Jianming Yang, Zunyuan Xie, Weiqiang Zhang
Format: Article
Language:English
Published: MDPI AG 2020-03-01
Series:Catalysts
Subjects:
<i>α</i>
<i>β</i>-alkynone
pd-catalyzed c−c coupling
<i>π</i>-acidicity
Online Access:https://www.mdpi.com/2073-4344/10/3/302
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spelling doaj-c85235b36f39439a8c3734551e60a7f12020-11-25T01:15:20ZengMDPI AGCatalysts2073-43442020-03-0110330210.3390/catal10030302catal10030302α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling ReactionMeng Guo0Zhen Wei1Jianming Yang2Zunyuan Xie3Weiqiang Zhang4Key Laboratory of Applied Surface and Colloid Chemistry MOE, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710119, ChinaKey Laboratory of Applied Surface and Colloid Chemistry MOE, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710119, ChinaXi′an Modern Chemistry Research Institute, Xi’an 710065, ChinaKey Laboratory of Applied Surface and Colloid Chemistry MOE, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710119, ChinaKey Laboratory of Applied Surface and Colloid Chemistry MOE, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710119, ChinaIn the palladium-catalyzed C&#8722;C coupling reaction, electron-rich phosphine ligands and a catalytic amount of catalyst loading are required in most cases. Herein, a bench-stable, easily modified and less toxic alkynone was utilized in palladium-catalyzed Sonogashira coupling to replace conventional phosphine ligands. With 1-(4-methoxyphenyl)-3-phenyl-2-yn-1-one (<b>L<sub>2</sub></b>) as the ligand, catalyst loading was reduced to 5-10 ppm. In this newly developed catalytic system, a variety of (hetero)arene iodines and alkynes could be tolerated, resulting in good yields of the corresponding cross-coupling products.https://www.mdpi.com/2073-4344/10/3/302<i>α</i><i>β</i>-alkynonepd-catalyzed c−c coupling<i>π</i>-acidicity
collection DOAJ
language English
format Article
sources DOAJ
author Meng Guo
Zhen Wei
Jianming Yang
Zunyuan Xie
Weiqiang Zhang
spellingShingle Meng Guo
Zhen Wei
Jianming Yang
Zunyuan Xie
Weiqiang Zhang
α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction
Catalysts
<i>α</i>
<i>β</i>-alkynone
pd-catalyzed c−c coupling
<i>π</i>-acidicity
author_facet Meng Guo
Zhen Wei
Jianming Yang
Zunyuan Xie
Weiqiang Zhang
author_sort Meng Guo
title α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction
title_short α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction
title_full α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction
title_fullStr α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction
title_full_unstemmed α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction
title_sort α, β-alkynone accelerated ppm level pd-catalyzed sonogashira coupling reaction
publisher MDPI AG
series Catalysts
issn 2073-4344
publishDate 2020-03-01
description In the palladium-catalyzed C&#8722;C coupling reaction, electron-rich phosphine ligands and a catalytic amount of catalyst loading are required in most cases. Herein, a bench-stable, easily modified and less toxic alkynone was utilized in palladium-catalyzed Sonogashira coupling to replace conventional phosphine ligands. With 1-(4-methoxyphenyl)-3-phenyl-2-yn-1-one (<b>L<sub>2</sub></b>) as the ligand, catalyst loading was reduced to 5-10 ppm. In this newly developed catalytic system, a variety of (hetero)arene iodines and alkynes could be tolerated, resulting in good yields of the corresponding cross-coupling products.
topic <i>α</i>
<i>β</i>-alkynone
pd-catalyzed c−c coupling
<i>π</i>-acidicity
url https://www.mdpi.com/2073-4344/10/3/302
work_keys_str_mv AT mengguo abalkynoneacceleratedppmlevelpdcatalyzedsonogashiracouplingreaction
AT zhenwei abalkynoneacceleratedppmlevelpdcatalyzedsonogashiracouplingreaction
AT jianmingyang abalkynoneacceleratedppmlevelpdcatalyzedsonogashiracouplingreaction
AT zunyuanxie abalkynoneacceleratedppmlevelpdcatalyzedsonogashiracouplingreaction
AT weiqiangzhang abalkynoneacceleratedppmlevelpdcatalyzedsonogashiracouplingreaction
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