Related Experiment Video
Updated: Mar 28, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Bismuth Undecahydro-closo-dodecaborane: A Retainable Intermediate of B-H Bond Activation by Bismuth(III) Cations
Lucas W Zimmermann1, Nguyen-Duc Van1, Dietrich Gudat1
1Institut für Anorganische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569, Stuttgart, Germany.
Abstract:
The [B12 H12](2-) anion shows an extensive substitutional chemistry based on its three-dimensional aromaticity. The replacement of functional groups can be attained by electrophilically induced substitution caused by Brønsted or Lewis acidic electrophiles (e.g. Pt(2+)). Until now, it was impossible to structurally characterize a metal-substituted [B12 H12](2-) cage. When an aqueous solution containing both Bi(3+) cations and [B12 H12](2-) anions was heated, the charge-neutral bismuth undecahydro-closo-dodecaborane BiB12 H11 was obtained, representing a new class of metalated [B12 H12](2-) clusters. The title compound was characterized by single-crystal X-ray diffraction and NMR spectroscopic methods. Compared to the typical B-H bond, the short B-Bi single bond (230 pm) exhibits inverted polarity.
More Related Videos
09:09A Facile Synthetic Method to Obtain Bismuth Oxyiodide Microspheres Highly Functional for the Photocatalytic Processes of Water Depuration
Published on: March 29, 2019
08:46Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
Related Concept Videos
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
Hydroboration-Oxidation of Alkenes
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.