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Peer-reviewedCC BY-NC 3.0Chemical Science

Modular synthesis of functionalized azetidines through visible-light copper-catalyzed carboamination of 1,3-dienes with azabicyclo[1.1.0]butanes

  • Yejin Koo1,2
  • Dongwoo Lee1,2
  • Jiyong Park1,2
  • Sungwoo Hong2,1
  1. 1Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST) Daejeon 34141 Korea
  2. 2Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS) Daejeon 34141 Korea
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Abstract

The strain-release reactivity of azabicyclo[1.1.0]butanes (ABBs) offers a powerful entry to substituted azetidines, yet modular access to highly functionalized, allylic amine-containing frameworks remains underdeveloped. Here, we report a visible-light copper-catalyzed four-component coupling that effects 1,4-carboamination of aryl-substituted 1,3-dienes, assembling azetidines bearing a quaternary carbon center from dienes, aryl amines, and electrophiles using ABBs. Synergistic copper/photoredox catalysis unites strain-release generation of an azetidinyl radical with allylic C–N bond formation, delivering densely functionalized azetidines bearing an allylic amine in a single, redox-neutral operation. The reaction proceeds with high 1,4-regioselectivity and broad functional-group tolerance across diverse anilines, ABBs, dienes, and electrophiles, and operates under mild conditions. Biorelevant complex-molecule diversification, scalability, and downstream derivatization underscore the synthetic utility of the platform, while DFT calculations trace the 1,4-selectivity to stabilizing noncovalent interactions that favor benzylic C–N coupling and steric repulsion that disfavors the competing pathway.

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Cite

BibTeXRIS
BibTeX
@article{koo2026modular,
  title = {{Modular synthesis of functionalized azetidines through visible-light copper-catalyzed carboamination of 1,3-dienes with azabicyclo[1.1.0]butanes}},
  author = {Yejin Koo and Dongwoo Lee and Jiyong Park and Sungwoo Hong},
  journal = {Chemical Science},
  year = {2026},
  month = aug,
  doi = {10.1039/d6sc06133h},
  url = {https://doi.org/10.1039/d6sc06133h},
  note = {CC BY-NC 3.0},
}
RIS
TY  - JOUR
TI  - Modular synthesis of functionalized azetidines through visible-light copper-catalyzed carboamination of 1,3-dienes with azabicyclo[1.1.0]butanes
AU  - Yejin Koo
AU  - Dongwoo Lee
AU  - Jiyong Park
AU  - Sungwoo Hong
PY  - 2026
DA  - 2026/08/27
JO  - Chemical Science
DO  - 10.1039/d6sc06133h
UR  - https://doi.org/10.1039/d6sc06133h
AB  - The strain-release reactivity of azabicyclo[1.1.0]butanes (ABBs) offers a powerful entry to substituted azetidines, yet modular access to highly functionalized, allylic amine-containing frameworks remains underdeveloped. Here, we report a visible-light copper-catalyzed four-component coupling that effects 1,4-carboamination of aryl-substituted 1,3-dienes, assembling azetidines bearing a quaternary carbon center from dienes, aryl amines, and electrophiles using ABBs. Synergistic copper/photoredox catalysis unites strain-release generation of an azetidinyl radical with allylic C–N bond formation, delivering densely functionalized azetidines bearing an allylic amine in a single, redox-neutral operation. The reaction proceeds with high 1,4-regioselectivity and broad functional-group tolerance across diverse anilines, ABBs, dienes, and electrophiles, and operates under mild conditions. Biorelevant complex-molecule diversification, scalability, and downstream derivatization underscore the synthetic utility of the platform, while DFT calculations trace the 1,4-selectivity to stabilizing noncovalent interactions that favor benzylic C–N coupling and steric repulsion that disfavors the competing pathway.
SN  - 2041-6520
SN  - 2041-6539
ER  -