What is it about?

This paper introduces a new three-component chemical process that efficiently transforms inexpensive nitro compounds, boronic acids, and trialkyl phosphites into tertiary aromatic amines. The method is highly versatile, accommodating various chemical groups on nitro and boronic acid components. Its uniqueness lies in not requiring transition-metal catalysts, making it cost-effective and environmentally friendly. Additionally, it can work alongside other metal-catalyzed methods, enabling the synthesis of diverse compounds, including special types like α-amino ester derivatives. [Some of the contents of this page have been created with AI]

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Why is it important?

1. Sustainable and Transition-Metal-Free Synthesis: The paper introduces a novel method for synthesizing tertiary aryl amines without the need for transition-metal catalysts. Transition metals are often expensive and can pose environmental and toxicity concerns. The development of transition-metal-free reactions is, therefore, a significant advancement in the field of organic synthesis, contributing to more sustainable and eco-friendly practices. 2. Versatile Three-Component Reaction: The described three-component reaction is versatile, joining nitro compounds, boronic acids, and trialkyl phosphites. This versatility expands the scope of accessible tertiary aryl amines, providing a flexible and broadly applicable synthetic route. 3. Tolerance to Functional Groups: The method is reported to tolerate different functional groups, including halogens, esters, and other substituents. This tolerance enhances the compatibility of the reaction with diverse molecular structures, enabling the synthesis of a wide range of functionalized compounds. Eg, it has been applied to α-amino ester derivatives. 4. Application in Medicinal Chemistry: Tertiary aryl amines are important structural motifs found in various bioactive molecules and pharmaceuticals. The paper discusses the synthesis of N-alkyl diarylamines and α-amino esters, showcasing the potential applications of the developed method in medicinal chemistry and drug discovery. 5. Efficiency and Scalability: The presented reaction conditions are optimized for efficiency, and the authors demonstrate scalability by performing a 1 g-scale synthesis. This feature is crucial for practical applications in industry, where large-scale synthesis is often required. 6. Contribution to Sustainable Chemistry: The paper aligns with the growing emphasis on sustainable chemistry by proposing a transition-metal-free and scalable synthetic route. Sustainable methods are essential for minimizing the environmental impact of chemical processes in research and industry.


This paper contributes to the advancement of synthetic methodologies by providing an efficient, versatile, and sustainable approach to the synthesis of tertiary aryl amines, with potential applications in medicinal chemistry and beyond. The reaction's tolerance to various substituents, including compounds such as α-amino esters, suggests broad applications in bioactive molecule, pharmaceutical, and material synthesis. The emphasis on scalability, demonstrated through a successful 1 g-scale synthesis, indicates its potential for industrial applications. The paper is seen not only as a scientific contribution but also as a promising avenue for more sustainable and efficient chemical synthesis practices, inspiring researchers to adopt innovative and green approaches in their own work.

Professor Aurelio G CSAKY
Universidad Complutense de Madrid. Instituto Pluridisciplinar

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This page is a summary of: Transition‐Metal‐Free Three‐Component Synthesis of Tertiary Aryl Amines from Nitro Compounds, Boronic Acids, and Trialkyl Phosphites, Advanced Synthesis & Catalysis, November 2019, Wiley,
DOI: 10.1002/adsc.201901009.
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