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Iterative click reactions using trivalent platforms for sequential molecular assembly.

Gaku Orimoto1, Suguru Yoshida1

  • 1Department of Biological Science and Technology, Faculty of Advanced Engineering, Tokyo University of Science, 6-3-1 Niijuku, Katsushika-ku, Tokyo 125-8585, Japan. s-yoshida@rs.tus.ac.jp.

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A new method allows easy synthesis of multi(triazole)s using iterative click reactions. This approach tolerates various functional groups, enabling diverse molecule construction without complex transformations.

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Area of Science:

  • Organic Chemistry
  • Polymer Chemistry
  • Materials Science

Background:

  • Click chemistry enables efficient molecular assembly.
  • Iterative synthesis strategies are crucial for complex molecule construction.
  • Sulfur-fluoride exchange (SuFEx), CuAAC, and thia-Michael reactions are key click chemistry tools.

Purpose of the Study:

  • To develop a facile synthesis for multi(triazole)s.
  • To demonstrate the utility of iterative click reactions for creating diverse mid-molecules.
  • To showcase the functional group tolerance of sequential click assembly.

Main Methods:

  • Employing sequential click reactions including sulfur-fluoride exchange (SuFEx), copper-catalyzed azide-alkyne cycloaddition (CuAAC), and thia-Michael reaction.
  • Utilizing readily available building blocks for modular synthesis.
  • Performing chemoselective reactions without requiring functional group transformations.

Main Results:

  • Successful facile synthesis of multi(triazole)s achieved through iterative click reactions.
  • Demonstrated good functional group tolerance throughout the sequential click assembly process.
  • Produced diverse multi(triazole)-type mid-molecules efficiently.

Conclusions:

  • Iterative click reactions provide an accessible route to complex multi(triazole) structures.
  • The developed method offers high chemoselectivity and broad functional group compatibility.
  • This strategy simplifies the synthesis of diverse mid-molecules from simple precursors.