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PreprintCC BYChemRxiv

N-Phosphoryl Imines Enable Intermolecular Aza Paternò–Büchi Reactions with Unactivated and Activated Alkenes

  • Scott L. Kim1
  • Lillian J. Carleu2
  • Corinna S. Schindler3
  1. 1Department of Chemistry, University of British Columbia, 203 Main Mall, Vancouver, BC, Canada, V6T 1Z1
  2. 2Department of Biochemistry and Molecular Biology, University of British Columbia, 2350 Health Sciences Mall, Vancouver, BC, Canada, V6T 1Z3
  3. 3BC Cancer Research Institute, 675 West 10th Ave, Vancouver, BC, Canada, V5Z 1L3
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Abstract

Intermolecular aza Paternò–Büchi (aPB) reactions provide a direct and convergent approach to azetidines through the photocycloaddition of imines and alkenes. However, reactions involving unactivated alkenes remain challenging, particularly with acyclic imines, whose excited states are susceptible to rapid nonradiative relaxation and competing photochemical pathways. Here, we report N-phosphinyl imines as readily accessible and stable photoreactive partners for visiblelight-mediated intermolecular aPB reactions with unactivated alkenes. Triplet sensitization using thioxanthone as an inexpensive organic photocatalyst enables productive [2+2]-cycloaddition across a range of alkenes, establishing a new reagent platform for intermolecular aPB chemistry to expand the accessible reactivity of acyclic imines with unactivated alkenes.

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Cite

BibTeXRIS
BibTeX
@misc{kim2026nphosphoryl,
  title = {{N-Phosphoryl Imines Enable Intermolecular Aza Paternò–Büchi Reactions with Unactivated and Activated Alkenes}},
  author = {Scott L. Kim and Lillian J. Carleu and Corinna S. Schindler},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15007906/v2},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15007906/v2},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - N-Phosphoryl Imines Enable Intermolecular Aza Paternò–Büchi Reactions with Unactivated and Activated Alkenes
AU  - Scott L. Kim
AU  - Lillian J. Carleu
AU  - Corinna S. Schindler
PY  - 2026
DA  - 2026/09/20
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15007906/v2
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15007906/v2
AB  - Intermolecular aza Paternò–Büchi (aPB) reactions provide a direct and convergent approach to azetidines through the photocycloaddition of imines and alkenes. However, reactions involving unactivated alkenes remain challenging, particularly with acyclic imines, whose excited states are susceptible to rapid nonradiative relaxation and competing photochemical pathways. Here, we report N-phosphinyl imines as readily accessible and stable photoreactive partners for visiblelight-mediated intermolecular aPB reactions with unactivated alkenes. Triplet sensitization using thioxanthone as an inexpensive organic photocatalyst enables productive [2+2]-cycloaddition across a range of alkenes, establishing a new reagent platform for intermolecular aPB chemistry to expand the accessible reactivity of acyclic imines with unactivated alkenes.
ER  -