Pd-Catalyzed Aryl C-H Amination with Diaziridinone
Jianjun Wang1, Daguo Hu1, Xiaofeng Sun1
1Institute of Natural and Synthetic Organic Chemistry, Changzhou University, Changzhou 213164, China.
Organic Letters
|March 17, 2023
Summary
This study presents an efficient palladium-catalyzed ortho-C-H amination method using di-tert-butyldiaziridinone to synthesize diverse anthranilic amides. The reaction proceeds through a palladacycle intermediate, offering a valuable route for amide synthesis.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Palladium-catalyzed C-H activation is a powerful tool in organic synthesis.
- Efficient methods for synthesizing anthranilic amides are crucial for medicinal chemistry and materials science.
Purpose of the Study:
- To develop an efficient palladium-catalyzed ortho-C-H amination of N-(quinolin-8-yl)benzamides.
- To synthesize a variety of anthranilic amides using di-tert-butyldiaziridinone as the amine source.
Main Methods:
- The study employed palladium catalysis for ortho-C-H functionalization.
- N-(quinolin-8-yl)benzamides were reacted with di-tert-butyldiaziridinone under optimized conditions.
Main Results:
- An efficient Pd-catalyzed ortho-C-H amination was achieved.
- A variety of anthranilic amides were synthesized in good yields.
Conclusions:
- The developed method provides a facile and efficient route to valuable anthranilic amides.
- The reaction mechanism likely involves a palladacycle intermediate facilitating C-H activation and amination.
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