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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Structural Interconversion Based on Intramolecular Boroxine Formation.

Kosuke Ono¹, Keisuke Sawanaga¹, Satoru Onodera²

¹School of Science, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|April 24, 2023

Summary

This summary is machine-generated.

Researchers developed a novel intramolecular boroxine formation unit. A macrocyclic triboronic acid quantitatively forms a tricyclic boroxine through a temperature-controlled, entropically driven process.

Keywords:

boroxine dynamic interconversion entropic stabilization intramolecular boroxine formation macrocycles

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Published on: March 25, 2017

Area of Science:

Supramolecular Chemistry
Organic Chemistry
Materials Science

Background:

Boroxine formation is typically intermolecular.
Controlling boroxine formation for specific molecular architectures is challenging.
Macrocyclic structures offer unique possibilities for intramolecular reactions.

Purpose of the Study:

To develop a novel structural interconversion unit based on intramolecular boroxine formation.
To investigate the quantitative formation of a tricyclic boroxine from a macrocyclic triboronic acid.
To explore the dynamic and thermodynamic properties of this novel interconversion.

Main Methods:

Synthesis of a macrocyclic triboronic acid with phenylboronic acid units.
Investigation of boroxine formation under varying conditions (heating/cooling).
Thermodynamic analysis of the intramolecular versus intermolecular reaction pathways.

Main Results:

Quantitative formation of a tricyclic boroxine via intramolecular cyclization.
Demonstration of dynamic interconversion between macrocyclic triboronic acid and tricyclic boroxine.
Identification of an entropic advantage driving the intramolecular process.
High hydrolytic stability of the entropically stabilized tricyclic boroxine.

Conclusions:

A novel, entropically stabilized tricyclic boroxine has been synthesized.
Intramolecular boroxine formation can be quantitatively controlled in macrocyclic systems.
This system exhibits dynamic structural interconversion and high stability, offering potential applications in molecular design.