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Hydrophosphination of boron-boron multiple bonds
Tom E Stennett1,2, Arumugam Jayaraman1,2, Tobias Brückner1,2
1Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg Am Hubland 97074 Würzburg Germany h.braunschweig@uni-wuerzburg.de.
Five boron-boron multiple bond compounds react with diphenylphosphine without a catalyst. The reaction yields depend on the boron compound structure, with density functional theory explaining the different pathways.
Area of Science:
- Organoboron chemistry
- Catalysis
- Organic synthesis
Background:
- Boron-boron multiple bonds are reactive functional groups.
- Hydrophosphination is a key reaction for C-P and B-P bond formation.
- Catalyst-free reactions are desirable for sustainable chemistry.
Purpose of the Study:
- To investigate the hydrophosphination of compounds with boron-boron multiple bonds.
- To explore catalyst-free reaction conditions.
- To elucidate the reaction mechanisms and product selectivity.
Main Methods:
- Reaction of five different boron-boron compounds with diphenylphosphine.
- Analysis of reaction products using spectroscopic methods.
- Computational modeling using density functional theory (DFT) calculations.
Main Results:
- Five compounds containing boron-boron multiple bonds underwent hydrophosphination with diphenylphosphine without a catalyst.
- Product distribution varied based on the substitution pattern of the boron atoms in diborenes, yielding both 1,1- and 1,2-hydrophosphination products.
- A symmetrical diboryne underwent 1,2-hydrophosphination to form a hydro(phosphino)diborene.
- DFT calculations provided insights into the mechanistic pathways.
Conclusions:
- Catalyst-free hydrophosphination of boron-boron multiple bonds is feasible.
- The regioselectivity of the reaction is influenced by the substrate's structure.
- DFT calculations are valuable tools for understanding reaction mechanisms in organoboron chemistry.
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