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Infrared Irradiation-Assisted Green Approach for Pd-Catalyzed Buchwald-Hartwig Amination.

Ambra Maria Fiore1, Riccardo Ciciriello1, Davide Blasi1

  • 1Dipartimento di Chimica, Università degli Studi di Bari Aldo Moro, Via Edoardo Orabona 4, Bari, 70126, Italy.

Chemistry (Weinheim an Der Bergstrasse, Germany)
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Summary

This study introduces a green, infrared-assisted method for palladium-catalyzed Buchwald-Hartwig amination. This novel approach achieves moderate-to-good yields under mild conditions, simplifying C-N bond formation.

Keywords:
Buchwald–Hartwig aminationC–N bond formationgreen solventsinfrared irradiationquasi‐solvent‐free conditions

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Buchwald-Hartwig amination is a crucial reaction for C-N bond formation.
  • Traditional methods often require stringent conditions (anhydrous, inert atmosphere) and significant solvent use.
  • Developing sustainable and efficient catalytic systems remains a key challenge in organic synthesis.

Purpose of the Study:

  • To develop a novel, green, and efficient protocol for palladium-catalyzed Buchwald-Hartwig amination.
  • To explore the use of Infrared (IR) irradiation as an energy source for the reaction.
  • To conduct the reaction under simplified conditions, including quasi-solvent-free and open-air environments.

Main Methods:

  • Utilizing palladium catalysis for C-N coupling reactions.
  • Employing Infrared (IR) irradiation to drive the amination process.
  • Performing reactions under quasi-solvent-free conditions using cyclopentyl methyl ether and without excluding air.

Main Results:

  • Successful palladium-catalyzed Buchwald-Hartwig amination under IR irradiation.
  • Moderate-to-good yields achieved for C-N coupling reactions.
  • The protocol is effective with various aryl iodides and bromides (electron-donating and withdrawing groups) and diverse primary and secondary amines.

Conclusions:

  • The developed IR-assisted method offers a novel and green approach to Buchwald-Hartwig amination.
  • Simplified reaction conditions (quasi-solvent-free, nonanhydrous, open-air) enhance the practicality and sustainability of C-N coupling.
  • This protocol provides a valuable tool for efficient synthesis of arylamines.