Nickel‐Catalyzed Thiolation of Aryl Halides and Heteroaryl Halides through Electrochemistry

Transition‐metal‐catalyzed coupling reactions are useful tools for synthesizing aryl sulfur compounds. However, conventional transition‐metal‐catalyzed thiolation of aryl bromides and chlorides typically requires the use of strong base under elevated reaction temperature. Herein, we report the first...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-04, Vol.58 (15), p.5033-5037
Main Authors: Liu, Dong, Ma, Hong‐Xing, Fang, Ping, Mei, Tian‐Sheng
Format: Article
Language:English
Subjects:
Aromatic compounds
Bromides
Chemical reactions
Chemical synthesis
Chlorides
Coupling (molecular)
electrocatalysis
Electrochemical cells
Electrochemistry
electrosynthesis
Halides
Metals
Nickel
Sulfur
Sulfur compounds
Temperature requirements
thiolation
thiyl radicals
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Transition‐metal‐catalyzed coupling reactions are useful tools for synthesizing aryl sulfur compounds. However, conventional transition‐metal‐catalyzed thiolation of aryl bromides and chlorides typically requires the use of strong base under elevated reaction temperature. Herein, we report the first examples of nickel‐catalyzed electrochemical thiolation of aryl bromides and chlorides in the absence of an external base at room temperature using undivided electrochemical cells. It's electrifying! Nickel‐catalyzed thiolation of aryl halides was achieved in the absence of an external base and at room temperature through an electrochemical reaction in undivided electrochemical cells. This method provides a practical approach for the construction of aryl and heteroaryl C−S bonds.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201900956