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Updated: Jan 15, 2026
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Photochemical Ni-Catalyzed Selective Mono-N-Arylation
Geyang Song1, Ding-Zhan Nong1, Gang Li1
1Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
This study presents an efficient method for synthesizing N-monomethyl arylamines using a nickel catalyst and amine salts. The novel C-N coupling reaction avoids catalyst deactivation, offering a versatile approach for organic synthesis.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Selective synthesis of N-monomethyl arylamines is challenging.
- Small molecule amines can deactivate metal catalysts through coordination.
Purpose of the Study:
- To develop an efficient C-N coupling reaction for (hetero)aryl halides with small molecule amines.
- To prevent catalyst deactivation during the coupling reaction.
Main Methods:
- Utilized a bipyridine-Ni(II) complex as a catalyst.
- Employed purple light irradiation (390-395 nm) without a photosensitizer.
- Used small molecule amine salts and a soluble organic base.
Main Results:
- Achieved selective C-N coupling of (hetero)aryl halides with various methylamines and ethylamines.
- Demonstrated catalyst stability and prevention of deactivation.
- Showcased the reaction's feasibility and versatility with over 100 examples.
Conclusions:
- The developed Ni(I)-Ni(III) catalytic cycle provides an efficient route for N-monomethyl arylamine synthesis.
- This method offers a robust and versatile tool for organic synthesis applications.
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