Back to Search
Start Over
Superelectrophilic Activation of Phosphacoumarins towards Weak Nucleophiles via Brønsted Acid Assisted Brønsted Acid Catalysis.
- Source :
- International Journal of Molecular Sciences; Jun2024, Vol. 25 Issue 12, p6327, 16p
- Publication Year :
- 2024
-
Abstract
- The electrophilic activation of various substrates via double or even triple protonation in superacidic media enables reactions with extremely weak nucleophiles. Despite the significant progress in this area, the utility of organophosphorus compounds as superelectrophiles still remains limited. Additionally, the most common superacids require a special care due to their high toxicity, exceptional corrosiveness and moisture sensitivity. Herein, we report the first successful application of the "Brønsted acid assisted Brønsted acid" concept for the superelectrophilic activation of 2-hydroxybenzo[e][1,2]oxaphosphinine 2-oxides (phosphacoumarins). The pivotal role is attributed to the tendency of the phosphoryl moiety to form hydrogen-bonded complexes, which enables the formation of dicationic species and increases the electrophilicity of the phosphacoumarin. This unmasks the reactivity of phosphacoumarins towards non-activated aromatics, while requiring only relatively non-benign trifluoroacetic acid as the reaction medium. [ABSTRACT FROM AUTHOR]
- Subjects :
- BRONSTED acids
NUCLEOPHILES
SUPERACIDS
CATALYSIS
TRIFLUOROACETIC acid
Subjects
Details
- Language :
- English
- ISSN :
- 16616596
- Volume :
- 25
- Issue :
- 12
- Database :
- Complementary Index
- Journal :
- International Journal of Molecular Sciences
- Publication Type :
- Academic Journal
- Accession number :
- 178185755
- Full Text :
- https://doi.org/10.3390/ijms25126327