Rapid Access to a Cyclobutane-Containing Skeleton Fused with Chromane through In(III)-Catalyzed Intramolecular Annulation of 5-Hydroxy Benzochromene
Intramolecular oxidative annulation of 5-hydroxy benzochromene via In(OTf)<sub>3</sub> and DDQ catalysis, through an <i>ortho</i>-quinone methide radical intermediate, afforded various cyclobutane-containing products in good to excellent yields. This oxidative annulation pathway reveals great group tolerance and broad compatibility with benzochromene. In addition, this method exhibits an excellent ability to synthesize cyclobutane-containing products in gram-scale experiments, providing a novel approach to synthesize a series of natural products, such as cannabicyclol, isoeriobrucinol A, and ranhuadujuanine A.
Authors
- Yanting Che (ORCID: https://orcid.org/0000-0002-4480-6773)
- Hejiang Luo (ORCID: https://orcid.org/0009-0003-1465-2704)
- Fufang Wu (ORCID: https://orcid.org/0000-0002-3883-6132)
- Tao Jiang (ORCID: https://orcid.org/0000-0003-3715-5295)
- Rong‐Tao Li (ORCID: https://orcid.org/0000-0002-8100-8690)
- Rong Xie
Institutions
- Kunming University of Science and Technology (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-05-14
- DOI
- https://doi.org/10.1021/acs.orglett.5c01352
- Citations
- 5
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 4.68
Funders
- National Natural Science Foundation of China