Silaboration of [1.1.1]Propellane: A Storable Feedstock for Bicyclo[1.1.1]pentane Derivatives was written by Kondo, Masaki;Kanazawa, Junichiro;Ichikawa, Tomohiro;Shimokawa, Takumi;Nagashima, Yuki;Miyamoto, Kazunori;Uchiyama, Masanobu. And the article was included in Angewandte Chemie, International Edition in 2020.Electric Literature of C16H20B2N2O2 This article mentions the following:
The silaboration of [1.1.1]propellane enables direct introduction of B and Si functional groups onto the bicyclo[1.1.1]pentane (BCP) scaffold in high yield under mild, additive-free conditions. The silaborated BCP can be obtained on a gram-scale in a single step without the need for column-chromatog. purification, and is storable and easy to handle, providing a versatile synthetic intermediate for BCP derivatives We also describe various conversions of the C-B/C-Si bonds on the BCP scaffold, including development of a modified Suzuki-Miyaura cross-coupling reaction at the highly sterically hindered bridgehead sp3 carbon center of the BCP skeleton using a combination of highly activated BCP boronic esters, copper(I) oxide, and a PdCl2(dppf) catalyst system. 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: 1214264-88-6Electric Literature of C16H20B2N2O2).
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. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Electric Literature of C16H20B2N2O2
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts