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Intermolecular 2+2 imine-olefin photocycloadditions enabled by Cu(I)-alkene MLCT

Author

Listed:
  • Daniel M. Flores

    (University of California San Diego, Department of Chemistry and Biochemistry
    Element Biosciences)

  • Michael L. Neville

    (University of California San Diego, Department of Chemistry and Biochemistry)

  • Valerie A. Schmidt

    (University of California San Diego, Department of Chemistry and Biochemistry)

Abstract

2 + 2 Photocycloadditions are idealized, convergent construction approaches of 4-membered heterocyclic rings, including azetidines. However, methods of direct excitation are limited by the unfavorable photophysical properties of imines and electronically unbiased alkenes. Here, we report copper-catalyzed photocycloadditions of non-conjugated imines and alkenes to produce a variety of substituted azetidines. Design principles allow this base metal-catalyzed method to achieve 2 + 2 imine-olefin photocycloaddition via selective alkene activation through a coordination-MLCT pathway supported by combined experimental and computational mechanistic studies.

Suggested Citation

  • Daniel M. Flores & Michael L. Neville & Valerie A. Schmidt, 2022. "Intermolecular 2+2 imine-olefin photocycloadditions enabled by Cu(I)-alkene MLCT," Nature Communications, Nature, vol. 13(1), pages 1-6, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30393-6
    DOI: 10.1038/s41467-022-30393-6
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