Electrochemical Cross‐Coupling of C(sp2)−H with Aryldiazonium Salts via a Paired Electrolysis: an Alternative to Visible Light Photoredox‐Based Approach

Photoredox‐based C−H bond functionalization constitutes one of the most powerful and atom‐economical approaches to organic syntheses. During this type of reaction, single electron transfer takes place between the photocatalyst (PC) and redox‐ active substrates. Electrosynthesis also involves electro...

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Published in:Advanced synthesis & catalysis Vol. 361; no. 22; pp. 5170 - 5175
Main Authors: Jiang, Yang‐ye, Dou, Gui‐yuan, Zhang, Luo‐sha, Xu, Kun, Little, R. Daniel, Zeng, Cheng‐chu
Format: Journal Article
Language:English
Published: WEINHEIM Wiley 19.11.2019
Wiley Subscription Services, Inc
Subjects:
aryldiazonium salts
Chemistry
Chemistry, Applied
Chemistry, Organic
Cross coupling
Electrolysis
Electron transfer
Electrons
Hydrogen bonds
paired electrolysis
photoredox-based reactions
Photosynthesis
Physical Sciences
quinoxalin-2(1H)-ones
Science & Technology
Single electrons
Substrates
aryldiazonium salts
COMPLEX
HETEROARENES
photoredox-based reactions
paired electrolysis
cross-coupling
BOND FUNCTIONALIZATION
GENERATION
C-H FUNCTIONALIZATION
METAL-FREE
quinoxalin-2(1H)-ones
CATALYZED ARYLATION
ISSN:1615-4150, 1615-4169
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Abstract Photoredox‐based C−H bond functionalization constitutes one of the most powerful and atom‐economical approaches to organic syntheses. During this type of reaction, single electron transfer takes place between the photocatalyst (PC) and redox‐ active substrates. Electrosynthesis also involves electron transfer between substrates and electrodes. In this paper, we focus upon electrochemical cross‐coupling of C(sp2)−H with aryldiazonium salts and have developed an efficient electrochemical approach to the Minisci‐type arylation reaction. The constant current paired electrosynthesis proceeds in a simple undivided cell without external supporting electrolyte, features a wide range of substrates and is easy to scale‐up. These results demonstrate that photoredox‐based cross‐coupling of C(sp2)−H with aryldiazonium salts can also proceed successfully under paired electrolysis conditions, thereby contributing to understanding of the parallels between photosynthesis and electrosynthesis.
AbstractList Photoredox‐based C−H bond functionalization constitutes one of the most powerful and atom‐economical approaches to organic syntheses. During this type of reaction, single electron transfer takes place between the photocatalyst (PC) and redox‐ active substrates. Electrosynthesis also involves electron transfer between substrates and electrodes. In this paper, we focus upon electrochemical cross‐coupling of C(sp2)−H with aryldiazonium salts and have developed an efficient electrochemical approach to the Minisci‐type arylation reaction. The constant current paired electrosynthesis proceeds in a simple undivided cell without external supporting electrolyte, features a wide range of substrates and is easy to scale‐up. These results demonstrate that photoredox‐based cross‐coupling of C(sp2)−H with aryldiazonium salts can also proceed successfully under paired electrolysis conditions, thereby contributing to understanding of the parallels between photosynthesis and electrosynthesis.
Photoredox‐based C−H bond functionalization constitutes one of the most powerful and atom‐economical approaches to organic syntheses. During this type of reaction, single electron transfer takes place between the photocatalyst ( PC ) and redox‐ active substrates. Electrosynthesis also involves electron transfer between substrates and electrodes. In this paper, we focus upon electrochemical cross‐coupling of C( sp 2 )−H with aryldiazonium salts and have developed an efficient electrochemical approach to the Minisci‐type arylation reaction. The constant current paired electrosynthesis proceeds in a simple undivided cell without external supporting electrolyte, features a wide range of substrates and is easy to scale‐up. These results demonstrate that photoredox‐based cross‐coupling of C( sp 2 )−H with aryldiazonium salts can also proceed successfully under paired electrolysis conditions, thereby contributing to understanding of the parallels between photosynthesis and electrosynthesis. magnified image
Photoredox-based C-H bond functionalization constitutes one of the most powerful and atom-economical approaches to organic syntheses. During this type of reaction, single electron transfer takes place between the photocatalyst (PC) and redox- active substrates. Electrosynthesis also involves electron transfer between substrates and electrodes. In this paper, we focus upon electrochemical cross-coupling of C(sp(2))-H with aryldiazonium salts and have developed an efficient electrochemical approach to the Minisci-type arylation reaction. The constant current paired electrosynthesis proceeds in a simple undivided cell without external supporting electrolyte, features a wide range of substrates and is easy to scale-up. These results demonstrate that photoredox-based cross-coupling of C(sp(2))-H with aryldiazonium salts can also proceed successfully under paired electrolysis conditions, thereby contributing to understanding of the parallels between photosynthesis and electrosynthesis.
Author Xu, Kun
Zhang, Luo‐sha
Jiang, Yang‐ye
Zeng, Cheng‐chu
Little, R. Daniel
Dou, Gui‐yuan
Author_xml – sequence: 1
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  fullname: Xu, Kun
  organization: Beijing University of Technology
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  givenname: R. Daniel
  surname: Little
  fullname: Little, R. Daniel
  organization: University of California, Santa Barbara
– sequence: 6
  givenname: Cheng‐chu
  surname: Zeng
  fullname: Zeng, Cheng‐chu
  email: zengcc@bjut.edu.cn
  organization: Beijing University of Technology
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Keywords aryldiazonium salts
COMPLEX
HETEROARENES
photoredox-based reactions
paired electrolysis
cross-coupling
BOND FUNCTIONALIZATION
GENERATION
C-H FUNCTIONALIZATION
METAL-FREE
quinoxalin-2(1H)-ones
CATALYZED ARYLATION
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Snippet Photoredox‐based C−H bond functionalization constitutes one of the most powerful and atom‐economical approaches to organic syntheses. During this type of...
Photoredox-based C-H bond functionalization constitutes one of the most powerful and atom-economical approaches to organic syntheses. During this type of...
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SubjectTerms aryldiazonium salts
Chemistry
Chemistry, Applied
Chemistry, Organic
Cross coupling
Electrolysis
Electron transfer
Electrons
Hydrogen bonds
paired electrolysis
photoredox-based reactions
Photosynthesis
Physical Sciences
quinoxalin-2(1H)-ones
Science & Technology
Single electrons
Substrates
Title Electrochemical Cross‐Coupling of C(sp2)−H with Aryldiazonium Salts via a Paired Electrolysis: an Alternative to Visible Light Photoredox‐Based Approach
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fadsc.201901011
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Volume 361
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