Protonation-Enhanced Reactivity of Triplet State in Dearomative Photocycloaddition of Quinolines to Olefins
- Resource Type
- Authors
- Youhei Chitose; Tatsuya Morofuji; Manabu Abe; Shota Nagai; Naokazu Kano
- Source
- Organic letters. 23(16)
- Subject
- Bicyclic molecule
Computational chemistry
Chemistry
Energy transfer
Organic Chemistry
Intermolecular force
Reactivity (chemistry)
Protonation
Physical and Theoretical Chemistry
Triplet state
Biochemistry
Cycloaddition
- Language
- ISSN
- 1523-7052
The intermolecular dearomative cycloaddition of acidified bicyclic azaarenes with olefins was recently reported. We report here the crucial role of the acid in the dearomative photocycloaddition of quinolines to olefins. Experimental and theoretical results show that the key role of the protonation of quinolines is not to promote the energy transfer but to enhance the reactivity of the triplet state of quinolines toward olefins.