Iron-Catalyzed Radical-Mediated 1,3-Azidoalkylation of Bicyclo[1.1.0]butanes: Access to 1,1,3,3-Tetrasubstituted Cyclobutanes via Strain Release
Abstract
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 3 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.
Fields of Study & Subjects
Radical Photochemical Reactions
Catalytic C–H Functionalization Methods
Click Chemistry and Applications
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 9
- Pages
- 2836–2841
- Publication date
- 25 February 2026
- Language
- EN