Visible Light-Promoted Construction of Cage-Like Frameworks by Sequential [2 + 2] Cycloaddition
A sequential [2 + 2] cycloaddition of unsaturated <i>N</i>-acylindoles was developed under visible light irradiation in the presence of a photosensitizer, forming unprecedented cage-like medium-ring frameworks in high yields. By exploiting the distinct reactivity and selectivity of two types of olefins within the substrate, the transformation provides a single-step and atom-economical approach to such molecules with exclusive regio- and diastereoselectivity, excellent functional group tolerance, and mild reaction conditions. Experimental mechanistic and calculation studies suggest that this reaction proceeds through an energy transfer pathway in this double [2 + 2] cycloaddition process.
Authors
- Martin D. Smith (ORCID: https://orcid.org/0000-0002-8849-488X)
- Jianfu Chen (ORCID: https://orcid.org/0000-0001-5388-1524)
- Wenjun Tang (ORCID: https://orcid.org/0000-0002-8209-4156)
- Zhou Zhang (ORCID: https://orcid.org/0000-0003-2906-9450)
- Feng Yu (ORCID: https://orcid.org/0000-0002-6141-8158)
- Xiangqian Liu (ORCID: https://orcid.org/0000-0001-5918-1297)
- Kang Du (ORCID: https://orcid.org/0000-0001-6778-4733)
Institutions
- Mansfield University (US)
- East China University of Science and Technology (CN)
- Chinese Academy of Sciences (CN)
- Oxford Research Group (GB)
- Shanghai Institute of Organic Chemistry (CN)
- Institute for Advanced Study (DE)
- University of Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-21
- DOI
- https://doi.org/10.1021/acs.orglett.5c02023
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- National Key Research and Development Program of China