Closed-Loop Sulfur Dioxide Utilization in Photocatalytic Smiles Rearrangement
Radical-mediated Smiles rearrangement has been established as a robust methodology for forming C-C bonds via intramolecular radical cyclization and cleavage under mild conditions. Herein, we present an unprecedented closed-loop sulfur dioxide utilization in a photocatalytic Smiles rearrangement. This methodology enables efficient access to sulfone derivatives through an economical and environmentally benign protocol, exhibiting excellent compatibility with diverse substrates. Mechanistic investigations reveal that both alkyl and sulfonyl radicals act as crucial intermediates in this reaction.
Authors
- Chao Xie (ORCID: https://orcid.org/0000-0001-6197-2506)
- Dayong Shi (ORCID: https://orcid.org/0000-0001-8941-5285)
- Xing Pan (ORCID: https://orcid.org/0000-0002-8997-7840)
- Wenlong Shan
- Cong Shi (ORCID: https://orcid.org/0009-0000-5681-3834)
- Hongyun Qin (ORCID: https://orcid.org/0000-0003-4531-8330)
- Xiangqian Li (ORCID: https://orcid.org/0000-0002-5807-5633)
- Zemin Wang (ORCID: https://orcid.org/0000-0002-2660-3876)
- Ruihua Liu (ORCID: https://orcid.org/0000-0002-3586-4066)
- Jiashu Chen (ORCID: https://orcid.org/0000-0003-3222-1628)
- Jiqiang Zhu (ORCID: https://orcid.org/0009-0000-8248-6996)
- Wenli Zhuang
- Chenxia Gao
Institutions
- Shandong University (CN)
- Qingdao National Laboratory for Marine Science and Technology (CN)
- Kai Biotech (South Korea) (KR)
- State Key Laboratory of Microbial Technology
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-06
- DOI
- https://doi.org/10.1021/acs.orglett.5c01646
- Citations
- 4
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- Department of Science and Technology of Shandong Province
- Natural Science Foundation of Shandong Province
- Shenzhen Fundamental Research Program
- Key Technology Research and Development Program of Shandong