Robust NHC-palladacycles-catalyzed Suzuki−Miyaura cross-coupling of amides via C-N activation

Robust NHC-palladacycles (NHC = N-heterocyclic carbene) were synthesized and exhibited high catalytic activity towards Suzuki−Miyaura cross-coupling reactions between inactive amides with N-acetyl/benzyl substituents and aryl boronic acids, producing diverse ketones in good to excellent yields. This...

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Main Authors:	Qinyue Deng, Qingshu Zheng, Bin Zuo, Tao Tu
Format:	Article
Language:	English
Published:	KeAi Communications Co. Ltd. 2020-06-01
Series:	Green Synthesis and Catalysis
Subjects:	Aryl boronic acids C-N activation Inactive amides NHC-Palladacycle Suzuki−Miyaura cross-coupling
Online Access:	http://www.sciencedirect.com/science/article/pii/S2666554920300089

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record_format	Article
spelling	doaj-28d0136a987e4517b339bbb3f4aed7072021-10-05T04:21:25ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492020-06-01117578Robust NHC-palladacycles-catalyzed Suzuki−Miyaura cross-coupling of amides via C-N activationQinyue Deng0Qingshu Zheng1Bin Zuo2Tao Tu3Department of Chemistry, Fudan University, Shanghai 200438, China; College of Science, University of Shanghai for Science and Technology, Shanghai 200093, ChinaDepartment of Chemistry, Fudan University, Shanghai 200438, ChinaCollege of Science, University of Shanghai for Science and Technology, Shanghai 200093, ChinaDepartment of Chemistry, Fudan University, Shanghai 200438, China; Corresponding author.Robust NHC-palladacycles (NHC = N-heterocyclic carbene) were synthesized and exhibited high catalytic activity towards Suzuki−Miyaura cross-coupling reactions between inactive amides with N-acetyl/benzyl substituents and aryl boronic acids, producing diverse ketones in good to excellent yields. This unprecedented and practical palladacycles-catalyzed Suzuki−Miyaura cross-coupling of amides with boronic acids via selective C-N bond activation was attributed to the strong σ-donor and weak π-acceptor properties of acenaphthoimidazolylidene, which may highlight their potential in other challenging coupling transformations involving inactive amides.http://www.sciencedirect.com/science/article/pii/S2666554920300089Aryl boronic acidsC-N activationInactive amidesNHC-PalladacycleSuzuki−Miyaura cross-coupling
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Qinyue Deng Qingshu Zheng Bin Zuo Tao Tu
spellingShingle	Qinyue Deng Qingshu Zheng Bin Zuo Tao Tu Robust NHC-palladacycles-catalyzed Suzuki−Miyaura cross-coupling of amides via C-N activation Green Synthesis and Catalysis Aryl boronic acids C-N activation Inactive amides NHC-Palladacycle Suzuki−Miyaura cross-coupling
author_facet	Qinyue Deng Qingshu Zheng Bin Zuo Tao Tu
author_sort	Qinyue Deng
title	Robust NHC-palladacycles-catalyzed Suzuki−Miyaura cross-coupling of amides via C-N activation
title_short	Robust NHC-palladacycles-catalyzed Suzuki−Miyaura cross-coupling of amides via C-N activation
title_full	Robust NHC-palladacycles-catalyzed Suzuki−Miyaura cross-coupling of amides via C-N activation
title_fullStr	Robust NHC-palladacycles-catalyzed Suzuki−Miyaura cross-coupling of amides via C-N activation
title_full_unstemmed	Robust NHC-palladacycles-catalyzed Suzuki−Miyaura cross-coupling of amides via C-N activation
title_sort	robust nhc-palladacycles-catalyzed suzuki−miyaura cross-coupling of amides via c-n activation
publisher	KeAi Communications Co. Ltd.
series	Green Synthesis and Catalysis
issn	2666-5549
publishDate	2020-06-01
description	Robust NHC-palladacycles (NHC = N-heterocyclic carbene) were synthesized and exhibited high catalytic activity towards Suzuki−Miyaura cross-coupling reactions between inactive amides with N-acetyl/benzyl substituents and aryl boronic acids, producing diverse ketones in good to excellent yields. This unprecedented and practical palladacycles-catalyzed Suzuki−Miyaura cross-coupling of amides with boronic acids via selective C-N bond activation was attributed to the strong σ-donor and weak π-acceptor properties of acenaphthoimidazolylidene, which may highlight their potential in other challenging coupling transformations involving inactive amides.
topic	Aryl boronic acids C-N activation Inactive amides NHC-Palladacycle Suzuki−Miyaura cross-coupling
url	http://www.sciencedirect.com/science/article/pii/S2666554920300089
work_keys_str_mv	AT qinyuedeng robustnhcpalladacyclescatalyzedsuzukimiyauracrosscouplingofamidesviacnactivation AT qingshuzheng robustnhcpalladacyclescatalyzedsuzukimiyauracrosscouplingofamidesviacnactivation AT binzuo robustnhcpalladacyclescatalyzedsuzukimiyauracrosscouplingofamidesviacnactivation AT taotu robustnhcpalladacyclescatalyzedsuzukimiyauracrosscouplingofamidesviacnactivation
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Robust NHC-palladacycles-catalyzed Suzuki−Miyaura cross-coupling of amides via C-N activation

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