Iron-Catalyzed Radical-Mediated 1,3-Azidoalkylation of Bicyclo[1.1.0]butanes: Access to 1,1,3,3-Tetrasubstituted Cyclobutanes via Strain Release
An iron-catalyzed proton-coupled electron transfer (PCET)-mediated radical 1,3-azidoalkylation of bicyclo[1.1.0]butanes (BCBs) with diazo compounds and TMSN<sub>3</sub> is presented. Iron-catalyzed PCET activates diazo compounds to generate alkyl radicals rather than the more common carbenes. These radicals undergo addition to BCBs, followed by iron-mediated azide transfer, affording highly functionalized 1,1,3,3-tetrasubstituted cyclobutanes with good yields and stereoselectivity.
Authors
- Lei Guo (ORCID: https://orcid.org/0000-0003-2055-7618)
- Shanghui Tian
- Pei Li (ORCID: https://orcid.org/0000-0001-8699-8825)
- Kuan Zhang (ORCID: https://orcid.org/0009-0005-2878-4542)
- Xin-Hua Duan
Institutions
- Frontier Science Foundation (CH)
- Institute of Science and Technology
- Xi'an Jiaotong University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-02-25
- DOI
- https://doi.org/10.1021/acs.orglett.5c05275
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00