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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

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Efficient kinetic macrocyclization.

Wen Feng¹, Kazuhiro Yamato, Liuqing Yang

¹College of Chemistry, Key Laboratory for Radiation Physics and Technology of Ministry of Education, and Institute of Nuclear Science and Technology, Sichuan University, Chengdu, 610064, Sichuan, China.

Journal of the American Chemical Society

|February 5, 2009

Summary

This summary is machine-generated.

Researchers achieved highly efficient synthesis of large aromatic oligoamide macrocycles. Precursor folding and steric effects explain the high yields in these kinetic macrocyclization reactions, yielding large, shape-persistent structures.

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Area of Science:

Supramolecular Chemistry
Organic Synthesis
Materials Science

Background:

Kinetically controlled macrocyclization reactions typically yield poor results.
Backbone-rigidified oligoamides can adopt well-defined conformations.
Previous work demonstrated oligoamides forming crescent conformations.

Purpose of the Study:

To investigate the highly efficient formation of aromatic oligoamide macrocycles.
To understand the mechanism behind the unexpectedly high yields.
To synthesize large macrocycles with significant internal cavities.

Main Methods:

Synthesis of aromatic oligoamide macrocycles with six meta-linked residues.
Kinetic simulation and experimental coupling of oligoamide precursors.
One-step, multicomponent macrocyclization reactions using meta-diamines and para-diacid chlorides.

Main Results:

Macrocycles formed in high yields, deviating from kinetic simulations.
Precursor folding and remote steric effects were identified as key factors.
Large macrocycles (70-90 membered rings) with cavities up to 2.9 nm were synthesized efficiently (>80% yield).

Conclusions:

The study presents a rare, highly efficient kinetic macrocyclization system.
Precursor conformation and steric effects are crucial for efficient macrocycle formation.
This method yields large, shape-persistent macrocycles with potential applications.