Revisiting the Bench Stability of B2pin2
Abstract
Abstract Bis(pinacolato)diboron (B2pin2) is a widely used diboron reagent for the installation of modular boryl groups and is generally regarded as bench stable. Here we show that trace impurities can initiate an autocatalytic process that promotes oxidative decomposition of B2pin2 in the solid state. Once initiated, this process renders B2pin2 susceptible to reaction with molecular oxygen and HO–Bpin, leading to degradation of bulk material. Notably, decomposition propagates under closed container conditions but is suppressed in loosely capped containers, consistent with the involvement of volatile components in the degradation process. These findings reveal an unexpected vulnerability in a widely used boron reagent and establish practical guidelines for its storage and handling.
Fields of Study & Subjects
Organoboron and organosilicon chemistry
Boron Compounds in Chemistry
Boron and Carbon Nanomaterials Research
Publication details
- Journal / source
- Organometallics
- Publisher
- American Chemical Society (ACS)
- Volume
- 45
- Issue
- 17
- Pages
- 2069–2073
- Publication date
- 16 July 2026
- Language
- EN