Wesley D. Hatcher, Vanaparthi Satheesh, Michael C. Young, Erik A. Romero
{"title":"Revisiting the Bench Stability of B2pin2","authors":"Wesley D. Hatcher, Vanaparthi Satheesh, Michael C. Young, Erik A. Romero","doi":"10.1021/acs.organomet.6c00167","DOIUrl":null,"url":null,"abstract":"<p>Bis(pinacolato)diboron (B<sub>2</sub>pin<sub>2</sub>)\r\nis a widely\r\nused diboron reagent for the installation of modular boryl groups\r\nand is generally regarded as bench stable. Here we show that trace\r\nimpurities can initiate an autocatalytic process that promotes oxidative\r\ndecomposition of B<sub>2</sub>pin<sub>2</sub> in the solid state.\r\nOnce initiated, this process renders B<sub>2</sub>pin<sub>2</sub> susceptible\r\nto reaction with molecular oxygen and HO–Bpin, leading to degradation\r\nof bulk material. Notably, decomposition propagates under closed container\r\nconditions but is suppressed in loosely capped containers, consistent\r\nwith the involvement of volatile components in the degradation process.\r\nThese findings reveal an unexpected vulnerability in a widely used\r\nboron reagent and establish practical guidelines for its storage and\r\nhandling.</p>","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"45 17","pages":"2069–2073"},"PeriodicalIF":2.4000,"publicationDate":"2026-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organometallics","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.organomet.6c00167","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2026/7/16 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
引用次数: 0
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.
期刊介绍：
Organometallics is the flagship journal of organometallic chemistry and records progress in one of the most active fields of science, bridging organic and inorganic chemistry. The journal publishes Articles, Communications, Reviews, and Tutorials (instructional overviews) that depict research on the synthesis, structure, bonding, chemical reactivity, and reaction mechanisms for a variety of applications, including catalyst design and catalytic processes; main-group, transition-metal, and lanthanide and actinide metal chemistry; synthetic aspects of polymer science and materials science; and bioorganometallic chemistry.
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