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Boosting Ring Strain and Lewis Acidity of Borirane: Synthesis, Reactivity and Density Functional Theory Studies of an Uncoordinated Arylborirane Fused to o ‐Carborane
- Source :
- Chemistry – A European Journal. 29
- Publication Year :
- 2022
- Publisher :
- Wiley, 2022.
-
Abstract
- Among the parent borirane, benzoborirene and ortho-dicarbadodecaborane-fused borirane, the latter possesses the highest ring strain and the highest Lewis acidity according to our density functional theory (DFT) studies. The synthesis of this class of compounds is thus considerably challenging. The existing examples require either a strong π-donating group or an extra ligand for B-coordination, which nevertheless suppresses or completely turns off the Lewis acidity. The title compound, which possesses both features, not only allows the 1,2-insertion of P=O, C=O or C≡N to proceed under milder conditions, but also enables the heretofore unknown dearomative 1,4-insertion of Ar-(C=O)- into a B-C bond. The fusion of strained molecular systems to an o-carborane cage shows great promise for boosting both the ring strain and acidity.
- Subjects :
- ddc:540
Organic Chemistry
General Chemistry
Catalysis
Subjects
Details
- ISSN :
- 15213765 and 09476539
- Volume :
- 29
- Database :
- OpenAIRE
- Journal :
- Chemistry – A European Journal
- Accession number :
- edsair.doi.dedup.....63b2074131f2bbdbe17863c09f76066a
- Full Text :
- https://doi.org/10.1002/chem.202203265