Related Experiment Video
Updated: Aug 1, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
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.
Abstract:
A novel structural interconversion unit based on intramolecular boroxine formation has been developed. A macrocyclic triboronic acid consisting of three phenylboronic acid units linked by covalent linkers preferentially underwent intramolecular rather than intermolecular boroxine formation, resulting in a quantitative formation of tricyclic boroxine. This structural transformation was accompanied by changes in the polarity, flexibility, and size of the molecule. Dynamic interconversion between the macrocyclic triboronic acid and the tricyclic boroxine was achieved by simple heating/cooling, whereas no boroxine formation occurred upon heating when three boronic acid units were not connected by linkers. Thermodynamic analysis revealed that the entropic advantage of the intramolecular boroxine formation process resulted in these unique features. The entropically stabilized tricyclic boroxine also shows high stability with respect to hydrolysis.
Related Concept Videos
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Hydroboration-Oxidation of Alkenes
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Radical Reactivity: Intramolecular vs Intermolecular
Cycloaddition Reactions: MO Requirements for Thermal Activation
Hybridization of Atomic Orbitals I

