Visible-Light-Induced Intramolecular Dehydrogenative Cyclization of <i>o</i>-Aryl Benzaldehydes
A visible-light-induced dehydrogenative cyclization of <i>o</i>-aryl benzaldehydes has been developed by using bench-stable <i>N</i>-aminopyridinium salt as both a HAT reagent and a mild oxidant, which affords a wide range of fluorenones with diverse substitution patterns in moderate to excellent yields. Furthermore, this protocol is applicable to the <i>de novo</i> synthesis of the natural product Nobilone. Mechanism investigation supports a photoinduced homocleavage of <i>N</i>-aminopyridinium salt and a radical chain process.
Authors
- Jipeng Qi
- Hongyu Guo (ORCID: https://orcid.org/0000-0002-8131-7987)
- Wei‐Yu Shi
- Rong Zhou (ORCID: https://orcid.org/0000-0002-0322-9199)
- Yizhou Zhao (ORCID: https://orcid.org/0009-0009-9440-4324)
- Rongfang Liu
Institutions
- Nankai University (CN)
- New York College of Traditional Chinese Medicine (US)
- Shanxi University of Traditional Chinese Medicine (CN)
- Taiyuan University of Technology (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-08-22
- DOI
- https://doi.org/10.1021/acs.joc.5c01675
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- People's Government of Shanxi Province