Photosensitizer-Free Photoinduced Ground-State Triplet Carbene-Assisted Persistent Aryloxy Radical Generation via Hydrogen Atom Transfer
The traditional intermolecular O-H insertion strategy is typically associated with the reactivity exhibited by the singlet spin state, or it can alter the spin state from triplet to singlet by hydrogen bonding. Herein, we report diazoarylidene succinimide that generates a persistent ground-state triplet carbene under visible light (Blue LED, 456 nm) without a photosensitizer. This triplet carbene undergoes an intramolecular O-H insertion via hydrogen atom transfer, forming a persistent aryloxy radical without altering its spin state and leading to biologically relevant 2<i>H</i>-chromenes.
Authors
- Ramakrishna G. Bhat (ORCID: https://orcid.org/0000-0002-7739-9553)
- Supriyo Santra (ORCID: https://orcid.org/0000-0003-4884-2250)
- Debashree Ghosh (ORCID: https://orcid.org/0000-0003-0726-7878)
- Debasish Laha (ORCID: https://orcid.org/0000-0002-2479-6467)
- Balu S. Navale (ORCID: https://orcid.org/0000-0001-7998-7503)
- Onkar S. Bankar
Institutions
- Indian Association for the Cultivation of Science (IN)
- Indian Institute of Science Education and Research Pune (IN)
- Nagpur Institute of Technology (IN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-07
- DOI
- https://doi.org/10.1021/acs.orglett.4c02717
- Citations
- 2
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- University Grants Commission
- Indian Institute of Science Education and Research Pune
- Science and Engineering Research Board