# An Organoborate Monoxide Radical

## TL;DR

Scientists created a stable organic boron monoxide radical that is highly stable and can act as a catalyst in chemical reactions.

## Contribution

The synthesis and characterization of a stable organic boron monoxide radical with unique functionalization and catalytic properties.

## Key findings

- The radical is stabilized by a triaryl-substituted boryl group and a K cation, remaining stable at room temperature.
- It can mediate NO coupling to form a boryl hyponitrite derivative and catalyze Sn–Sn coupling reactions.
- The radical dimerizes to form peroxide species when the K cation is fully encapsulated.

## Abstract

The boron monoxide
radical has emerged as a fascinating molecule
and a short-lived intermediate, previously observed only under matrix
isolation conditions. In this study, we report the successful synthesis
and characterization of a stable organic boron monoxide radical, achieved
through the reaction of a diboron (6) dianion with nitric oxide (NO).
This oxygen-centered radical is uniquely functionalized and stabilized
by a triaryl-substituted boryl group. Comprehensive characterization
was performed using various spectroscopic and structural techniques,
including electron paramagnetic resonance (EPR) spectroscopy and single-crystal
X-ray diffraction analysis. Remarkably, this oxygen-centered radical
is stabilized by the K cation and exhibits significant stability under
argon at room temperature, showing no self-dimerization even when
heated or exposed to UV light. However, it can dimerize to form peroxide
species when the K cation is fully encapsulated. Furthermore, it can
mimic transition-metal complexes by mediating NO coupling to form
a boryl hyponitrite (N2O2
2–) derivative. Finally, this boron monoxide radical also shows promising
catalytic potential in Sn–Sn coupling reactions.