Trans-Diborylation of Alkynes: Pseudo-Intramolecular Strategy Utilizing a Propargylic Alcohol Unit was written by Nagashima, Yuki;Hirano, Keiichi;Takita, Ryo;Uchiyama, Masanobu. And the article was included in Journal of the American Chemical Society in 2014.Quality Control of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine This article mentions the following:
Authors present the first trans-selective diborylation reaction of alkynes. By theor. calculation-assisted reaction anal., authors designed a pseudo-intramol. reaction of diboron, propargyl alc., and a base to facilitate B-B bond activation and C-B bond formation with high efficiency. This approach provides synthetically versatile and densely functionalized 4-borylated 1,2-oxaborol-2(5H)-oles (vinyldiboronates) in a straightforward manner. Detailed computational anal. showed that the directing alkoxide functionality markedly lowers the activation energy of B-C bond formation. In the experiment, the researchers used many compounds, for example, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6Quality Control of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine).
2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6) 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. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Quality Control of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts