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Aza-[4 + 2]-cycloaddition of benzocyclobutenones into isoquinolinone derivatives enabled by photoinduced regio-specific C–C bond cleavage

Author

Listed:
  • Liangkun Yang

    (Sichuan University)

  • Shiyang Li

    (Sichuan University)

  • Lichao Ning

    (Sichuan University)

  • Hansen Zhao

    (Sichuan University)

  • Liang Zhou

    (Sichuan University)

  • Weidi Cao

    (Sichuan University)

  • Xiaoming Feng

    (Sichuan University)

Abstract

The activation of C−C bond of benzocyclobutenones under mild reaction conditions remains a challenge. We herein report a photoinduced catalyst-free regio-specific C1−C8 bond cleavage of benzocyclobutenones, enabling the generation of versatile ortho-quinoid ketene methides for aza-[4 + 2]-cycloaddition with imines, which offers a facile route to isoquinolinone derivatives, including seven family members of protoberberine alkaloids, gusanlung A, B, D, 8-oxotetrahydroplamatine, tetrahydrothalifendine, tetrahydropalmatine, and xylopinine. Furthermore, the catalytic enantioselective version of this strategy is also realized by merging synergistic photocatalysis and chiral Lewis acid catalysis. Mechanistic studies provide compelling evidence to rationalize the photoisomerization/cycloaddition cascade process.

Suggested Citation

  • Liangkun Yang & Shiyang Li & Lichao Ning & Hansen Zhao & Liang Zhou & Weidi Cao & Xiaoming Feng, 2024. "Aza-[4 + 2]-cycloaddition of benzocyclobutenones into isoquinolinone derivatives enabled by photoinduced regio-specific C–C bond cleavage," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-55110-3
    DOI: 10.1038/s41467-024-55110-3
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    References listed on IDEAS

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    1. Jianyu Zhang & Xi Wang & Tao Xu, 2021. "Regioselective activation of benzocyclobutenones and dienamides lead to anti-Bredt bridged-ring systems by a [4+4] cycloaddition," Nature Communications, Nature, vol. 12(1), pages 1-8, December.
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