Visible light-driven dearomative meta-cycloadditions of 2-acetonaphthalenes via triplet energy transfer cascade

Pramod Rai, Sanghamitra Naik, Kriti Gupta, Kakoli Maji, Garima Jindal () and Biplab Maji ()
Additional contact information
Pramod Rai: Indian Institute of Science Education and Research Kolkata
Sanghamitra Naik: Indian Institute of Science Education and Research Kolkata
Kriti Gupta: Indian Institute of Science
Kakoli Maji: Indian Institute of Science Education and Research Kolkata
Garima Jindal: Indian Institute of Science
Biplab Maji: Indian Institute of Science Education and Research Kolkata

Nature Communications, 2025, vol. 16, issue 1, 1-13

Abstract: Abstract Dearomative cycloadditions (DACs) with ortho- and para-variants have been well documented under visible light-mediated triplet-triplet energy transfer (VLEnT) catalysis. The prospective [3 + 2] or the meta-DACs propelled via VLEnT catalysis remains elusive. Classically, meta-DACs are known under harsher UV irradiations and are symmetry allowed in the excited singlet potential energy surface. Herein, we report formal meta-DACs of 2-acetonaphthalenes propagated via a two-step VLEnT cascade circumventing the attainment of energetically higher singlet excited states. The photosensitizer selectively promotes the [4 + 2] cycloaddition followed by a contra-thermodynamic di-π-methane type skeleton rearrangement cascade. The DFT studies in conjugation with electrochemical, photoluminescence, kinetic, quadratic dependency, and control experiments support the VLEnT cascade. The described protocol delivers highly sp3-rich polycyclic frameworks in high yields with wide functional group tolerance. The inclusion of bioactive molecules and the establishment of a wide array of post-synthetic derivatizations further underscores the adaptability of the methodology for generating complex three-dimensional molecules.

Date: 2025
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-025-58285-5 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-58285-5

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-025-58285-5

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().