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A Base-Free Two-Coordinate Oxoborane.

Clement R P Millet¹, Dominic R Willcox¹, Gary S Nichol¹

¹EaStCHEM School of Chemistry, University of Edinburgh, Edinburgh, EH9 3FJ, United Kingdom.

Angewandte Chemie (International Ed. in English)

|November 18, 2024

Summary

This summary is machine-generated.

Researchers stabilized elusive oxoboranes (R-BO) using a Lewis acid, aluminum chloride (AlCl3), creating a unique base-free, two-coordinate species. This breakthrough allows for novel reactivity, leading to unprecedented boron heterocycles.

Keywords:

Boron Boroxine Carbonyl compounds Oxoborane multiple bonding

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Area of Science:

Organoboron chemistry
Main group chemistry
Lewis acid-base chemistry

Background:

Oxoboranes (R-BO) are highly reactive and transient, typically trimerizing into boroxines.
Existing stabilization methods involve Lewis bases, resulting in three-coordinate oxoboranes with altered properties.

Purpose of the Study:

To synthesize and characterize a stable, base-free, two-coordinate oxoborane.
To investigate the bonding and reactivity of this novel species.

Main Methods:

Isolation of a two-coordinate oxoborane as a Lewis adduct with aluminum chloride (AlCl3).
Spectroscopic characterization, including infrared spectroscopy to determine the ν11BO stretching frequency.
Computational analysis to understand bonding interactions and electronic properties.

Main Results:

A stable, base-free, two-coordinate oxoborane, Mes*BO-AlCl3, was successfully isolated.
A strong BO bond was confirmed by a ν11BO stretching frequency of 1843 cm⁻¹.
Computational studies revealed a highly polarized BO bond with some multiple bond character, enhancing Lewis acidity at boron and reducing oxygen basicity.

Conclusions:

Coordination with AlCl3 provides a novel route to stabilize two-coordinate oxoboranes without Lewis bases.
The unique electronic properties of Mes*BO-AlCl3 enable novel reactivity.
Reaction with phenyl azide (PhN3) yielded an unprecedented boron heterocycle, opening new avenues in boron chemistry.