Related Experiment Video
Updated: Feb 18, 2026

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
Published on: March 25, 2017
1,3,2-Diazaborole-derived carbene complexes of boron
Hunter P Hickox1, Yuzhong Wang, Kaitlin M Luedecke
1Department of Chemistry and the Center for Computational Chemistry, The University of Georgia, Athens, Georgia 30602-2556, USA. robinson@uga.edu.
Abstract:
Reaction of 2-bromo-1,3,2-diazaborole (1) with excess BBr3 induces 1,2-hydrogen migration, giving 1,3,2-diazaborole-derived carbene complexes of boron bromide (2). Compound 2 exists in a dynamic solution equilibrium with 1. The 1H NMR study shows that the equilibrium lies to the right side of the dissociation reaction of 2. Parallel reaction of 1 with excess BI3 gives the corresponding 1,3,2-diazaborole-derived carbene boron iodide complex (3). Notably, in contrast to 2, the dissociation reaction of 3 largely lies to the left side, favouring the formation of 3. The dynamic solution equilibrium behaviours of 2 and 3 are probed by both experimental and theoretical methods.
More Related Videos
19:58Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Related Concept Videos
Hydroboration-Oxidation of Alkenes
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.
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.
Carbocations
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Hybridization of Atomic Orbitals I