Year: 2026
Type: article
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.
Source: Organometallics
Institutions: University of California San Diego, University of Toledo
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Funders: National Science Foundation, University of Toledo, University of California, San Diego, Materials Research Science and Engineering Center, Harvard University, Division of Chemistry, Materials Research Science and Engineering Center, University of California, San Diego, National Science Foundation Graduate Research Fellowship Program
OpenAlex ID: W7168662883