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Electrochemical control enables high-concentration, one-pot macrolactonization.

Siying Mao1, Dengchao Wei1, Kun Xu1

  • 1College of Chemistry and Life Science, Beijing University of Technology Beijing 100124 China kunxu@bjut.edu.cn.

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Summary
This summary is machine-generated.

This study introduces an electrochemical macrolactonization method for synthesizing lactones at high concentrations. This novel approach overcomes limitations of traditional methods, enabling efficient macrolactone formation.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Synthetic Chemistry

Background:

  • Macrolactone synthesis traditionally requires high dilution to prevent oligomerization.
  • Existing methods face concentration limitations, hindering scalability and efficiency.

Purpose of the Study:

  • To develop a novel electrochemical macrolactonization protocol.
  • To enable macrolactone synthesis at significantly higher concentrations than conventional methods.

Main Methods:

  • Utilized an electrochemical approach with an iodide/PPh3 dual-mediation system.
  • Operated the reaction at a high substrate concentration of 50 mM.
  • Investigated the formation of an acyloxyphosphonium intermediate.

Main Results:

  • Successfully synthesized 5- to 21-membered lactones.
  • Demonstrated compatibility with O-, S-, and N-heteroatom functionalization.
  • Achieved efficient macrolactonization at high concentrations, suppressing oligomerization.

Conclusions:

  • The electrochemical protocol offers a scalable and efficient alternative for macrolactone synthesis.
  • The dual-mediation system and intermediate formation are key to high-concentration success.
  • This method expands synthetic possibilities for complex lactone structures.