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Practical and regioselective amination of arenes using alkyl amines
Alessandro Ruffoni1, Fabio Juliá1, Thomas D Svejstrup1
1School of Chemistry, University of Manchester, Manchester, UK.
Nature Chemistry
|April 24, 2019
Summary
This study introduces a photocatalysis method for direct carbon-nitrogen bond formation, creating aromatic amines from arenes and alkyl amines without pre-functionalization. This efficient synthesis benefits diverse chemical applications and material production.
Area of Science:
- Organic Chemistry
- Catalysis
- Materials Science
Background:
- Carbon-nitrogen bond formation is crucial for synthesizing high-value materials like pharmaceuticals and polymers.
- Current methods often require multi-step processes involving pre-functionalization of aromatic C-H bonds.
Purpose of the Study:
- To develop a direct and efficient method for synthesizing aromatic amines.
- To bypass the need for pre-functionalization in C-N bond formation.
Main Methods:
- Utilizing photocatalysis for the direct reaction of arenes and alkyl amines.
- Implementing a batch-to-flow protocol for scalable synthesis.
Main Results:
- Successful construction of aromatic amines via direct C-H functionalization.
- Demonstrated broad functional group tolerance and compatibility with complex molecules.
- Achieved multigram scale synthesis using a continuous flow process.
Conclusions:
- The developed photocatalytic strategy offers a streamlined approach to aromatic amine synthesis.
- This method serves as a versatile late-stage functionalization platform for diverse chemical entities.
- The process is applicable to pharmaceuticals, agrochemicals, polymers, and catalysts.
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