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February 27, 2026Organic Letters0 citations

Iron-Catalyzed Radical-Mediated 1,3-Azidoalkylation of Bicyclo1.1.0butanes: Access to 1,1,3,3-Tetrasubstituted Cyclobutanes via Strain Release

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STShanghui TianKZKuan ZhangPLPei Li

Key Points

  • To explore iron-catalyzed radical-mediated 1,3-azidoalkylation of bicyclo[1.1.0]butanes and synthesize tetrasubstituted cyclobutanes.
  • Employ iron-catalyzed proton-coupled electron transfer to activate diazo compounds.
  • Generate alkyl radicals for addition to bicyclo[1.1.0]butanes.
  • Conduct azide transfer followed by characterization of cyclobutane products.
  • Successfully synthesized 1,1,3,3-tetrasubstituted cyclobutanes with good yields.
  • Achieved high stereoselectivity in the cyclobutane products.
  • Demonstrated a new pathway for cyclobutane synthesis using radical-mediated processes.

Abstract

An iron-catalyzed proton-coupled electron transfer (PCET)-mediated radical 1,3-azidoalkylation of bicyclo1.1.0butanes (BCBs) with diazo compounds and TMSN3 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.

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Cite This Study

Tian et al. (2026) studied this question.

synapsesocial.com/papers/69a134dded1d949a99abe50dhttps://doi.org/10.1021/acs.orglett.5c05275
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