Alcohol-initiated dediazoniation of aryldiazonium ions to aryl radicals: a simple and efficient route to arylboronates was written by Zhang, Xiulian;Zhang, Zhicheng;Xie, Yongbin;Jiang, Yujie;Xu, Ruibo;Luo, Yuhui;Tao, Chuanzhou. And the article was included in Journal of Chemical Research in 2018.Reference of 68716-49-4 This article mentions the following:
A simple and efficient access to arylboronates was achieved with methanol-initiated borylation of aryldiazonium salts. Reduction of aryldiazonium ions by single electron transfer from methanol affords aryl radical species, which undergo a subsequent C-B bond formation with bis(pinacolato)diboron. This highly practical borylation process, which can be carried out on the gram-scale, enjoys operational simplicity as well as mild and catalyst-free conditions. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Reference of 68716-49-4).
2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Reference of 68716-49-4
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts