Related Experiment Video
Updated: Jun 8, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Group 3-centred dehydrocoupling of Me2NH·BH3
Michael S Hill1, Gabriele Kociok-Köhn, Thomas P Robinson
1Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK. msh27@bath.ac.uk
Group 3 metal amides react with dimethylamine borane to form amidoborane derivatives. This process also enables the dehydrogenative coupling of amine borane fragments under mild conditions.
Area of Science:
- Organometallic Chemistry
- Inorganic Chemistry
- Boron Chemistry
Background:
- Group 3 metals (Scandium, Yttrium) exhibit unique reactivity in coordination chemistry.
- Amine boranes are valuable precursors in synthetic chemistry and materials science.
- Dehydrogenative coupling reactions offer atom-economical pathways for forming new chemical bonds.
Purpose of the Study:
- To investigate the stoichiometric and catalytic reactions of Group 3 metal amides with dimethylamine borane.
- To explore the formation of amidoborane derivatives.
- To demonstrate the dehydrogenative coupling of amine borane fragments.
Main Methods:
- Reactions were conducted under mild conditions.
- Stoichiometric and catalytic approaches were employed using Group 3 (Sc, Y) amides.
- Dimethylamine borane (Me(2)NH·BH(3)) was used as the boron source.
Main Results:
- Formation of corresponding amidoborane derivatives was observed.
- Dehydrogenative coupling of two amine borane fragments was achieved.
- The reactions proceeded efficiently under the investigated conditions.
Conclusions:
- Group 3 metal amides are effective reagents for synthesizing amidoboranes.
- The methodology provides a mild route for amine borane dehydrogenative coupling.
- This work expands the synthetic utility of Group 3 metal complexes and amine boranes.
Related Concept Videos
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.
Diazonium Group Substitution: –OH and –H
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene
Hydroboration-Oxidation of Alkenes
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

