Cathodic Aromatic C,C Cross-Coupling Reaction via Single Electron Transfer Pathway

We have successfully developed a novel cathodic cross-coupling reaction of aryl halides with arenes. Utilization of the cathodic single electron transfer (SET) mechanism for activation of aryl halides enables the cross-coupling reaction to proceed without the need for any transition metal catalysts...

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Main Authors: Yang Qu, Hiroyuki Tateno, Yoshimasa Matsumura, Tsuneo Kashiwagi, Mahito Atobe
Format: Article
Language:English
Published: MDPI AG 2017-03-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/22/3/413
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author Yang Qu
Hiroyuki Tateno
Yoshimasa Matsumura
Tsuneo Kashiwagi
Mahito Atobe
author_facet Yang Qu
Hiroyuki Tateno
Yoshimasa Matsumura
Tsuneo Kashiwagi
Mahito Atobe
author_sort Yang Qu
collection DOAJ
description We have successfully developed a novel cathodic cross-coupling reaction of aryl halides with arenes. Utilization of the cathodic single electron transfer (SET) mechanism for activation of aryl halides enables the cross-coupling reaction to proceed without the need for any transition metal catalysts or single electron donors in a mild condition. The SET from a cathode to an aryl halide initiates a radical chain by giving an anion radical of the aryl halide. The following propagation cycle also consists entirely of anion radical intermediates.
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spelling doaj.art-83bf8457570e48b2a009f9b9d212f7512022-12-21T18:27:53ZengMDPI AGMolecules1420-30492017-03-0122341310.3390/molecules22030413molecules22030413Cathodic Aromatic C,C Cross-Coupling Reaction via Single Electron Transfer PathwayYang Qu0Hiroyuki Tateno1Yoshimasa Matsumura2Tsuneo Kashiwagi3Mahito Atobe4Graduate School of Environment and Information Sciences, Yokohama National University, 79-7, Tokiwadai, Hodogaya-ku, Yokohama 240851, JapanGraduate School of Environment and Information Sciences, Yokohama National University, 79-7, Tokiwadai, Hodogaya-ku, Yokohama 240851, JapanGraduate School of Environment and Information Sciences, Yokohama National University, 79-7, Tokiwadai, Hodogaya-ku, Yokohama 240851, JapanGraduate School of Environment and Information Sciences, Yokohama National University, 79-7, Tokiwadai, Hodogaya-ku, Yokohama 240851, JapanGraduate School of Environment and Information Sciences, Yokohama National University, 79-7, Tokiwadai, Hodogaya-ku, Yokohama 240851, JapanWe have successfully developed a novel cathodic cross-coupling reaction of aryl halides with arenes. Utilization of the cathodic single electron transfer (SET) mechanism for activation of aryl halides enables the cross-coupling reaction to proceed without the need for any transition metal catalysts or single electron donors in a mild condition. The SET from a cathode to an aryl halide initiates a radical chain by giving an anion radical of the aryl halide. The following propagation cycle also consists entirely of anion radical intermediates.http://www.mdpi.com/1420-3049/22/3/413electrochemical synthesissingle electron transferC,C cross-coupling
spellingShingle Yang Qu
Hiroyuki Tateno
Yoshimasa Matsumura
Tsuneo Kashiwagi
Mahito Atobe
Cathodic Aromatic C,C Cross-Coupling Reaction via Single Electron Transfer Pathway
Molecules
electrochemical synthesis
single electron transfer
C,C cross-coupling
title Cathodic Aromatic C,C Cross-Coupling Reaction via Single Electron Transfer Pathway
title_full Cathodic Aromatic C,C Cross-Coupling Reaction via Single Electron Transfer Pathway
title_fullStr Cathodic Aromatic C,C Cross-Coupling Reaction via Single Electron Transfer Pathway
title_full_unstemmed Cathodic Aromatic C,C Cross-Coupling Reaction via Single Electron Transfer Pathway
title_short Cathodic Aromatic C,C Cross-Coupling Reaction via Single Electron Transfer Pathway
title_sort cathodic aromatic c c cross coupling reaction via single electron transfer pathway
topic electrochemical synthesis
single electron transfer
C,C cross-coupling
url http://www.mdpi.com/1420-3049/22/3/413
work_keys_str_mv AT yangqu cathodicaromaticcccrosscouplingreactionviasingleelectrontransferpathway
AT hiroyukitateno cathodicaromaticcccrosscouplingreactionviasingleelectrontransferpathway
AT yoshimasamatsumura cathodicaromaticcccrosscouplingreactionviasingleelectrontransferpathway
AT tsuneokashiwagi cathodicaromaticcccrosscouplingreactionviasingleelectrontransferpathway
AT mahitoatobe cathodicaromaticcccrosscouplingreactionviasingleelectrontransferpathway