Substrate-Regulated Divergent Addition of <i>N</i>-Sulfonyl Ketimines to Bicyclo[1.1.0]butanes Enabled by Photoinduced Energy Transfer
A substrate-regulated divergent addition of <i>N</i>-sulfonyl ketimines to bicyclo[1.1.0]butanes (BCBs) was developed using a photoinduced energy transfer strategy. The [2π+2σ] cycloaddition of BCBs with saccharin-derived cyclic ketimines yields benzosultam-fused aza-BCHs with good yields and excellent diastereoselectivity. In contrast, reactions of chain <i>N</i>-sulfonyl ketimines with BCBs produce 1,3-fully substituted cyclobutanes via energy-transfer-induced N-S bond homolysis. The ease of large-scale synthesis and derivatizations of products highlight their application potentials.
Authors
- Li‐Na Guo (ORCID: https://orcid.org/0000-0002-9789-6952)
- Ruxue Liu
- Shanghui Tian
- Yinuo Liu (ORCID: https://orcid.org/0009-0008-7124-9328)
- Xin‐Hua Duan (ORCID: https://orcid.org/0000-0002-1527-5934)
- Pengfei Li (ORCID: https://orcid.org/0000-0002-4736-2477)
- Kuan Zhang (ORCID: https://orcid.org/0000-0002-4262-153X)
- Yan Xia (ORCID: https://orcid.org/0000-0002-9242-2213)
Institutions
- Frontier Science Foundation (CH)
- Institute of Science and Technology
- Xi'an Jiaotong University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-03
- DOI
- https://doi.org/10.1021/acs.orglett.5c00189
- Citations
- 13
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 12.17
Funders
- National Natural Science Foundation of China
- Fundamental Research Funds for the Central Universities